Subhash P. Chavan

Subhash P. Chavan

Organic Chemistry Division

About Me

The research in Dr. Chavan’s group focus on the synthesis of biologically active compounds which include natural products, non-natural products and hybrid molecules. Another aspect which this group involves is the development of synthetic methodologies including custom designed methodologies and its application towards the synthesis of organic molecules. Asymmetric synthesis of biologically active molecules involving chirons as well as asymmetric synthesis including organocatalysts. Development of non-infringing processes for commercially important molecules. Process development, Custom synthesis and development of new chemical entities for antifungal applications.

Professional Experience

1) Sci-G:  August 2010-till date, CSIR-National Chemical Laboratory, Pune, India

2) Sci-F: August 2005 -2010, Organic Chemistry: Technology, NCL, Pune: 411 008, India

3) Sci-E-II, E-1 & #C: August 2000-2005, 1995-2000 & 1990-95, Organic Chemistry: Division, NCL, Pune: 411 008, India

4) Sc. Fellow: August 1989 - 1991, NCL, Pune: 411 008, India

5) Post-doc: Jan. 1986 - 1989, University of Minnesota, USA

    Advisor: Prof. Paul G. Gassman

6) Ph. D.: 1981 - 1985, National Chemical Laboratory, Pune :411 008, India. 

    Advisor: Dr. A. V. Rama Rao

7) M. Sc.: 1981, (Organic Chemistry) Department of Chemistry, University of Poona, Pune: 411 007, India

8) B.Sc.: 1979 (Chemistry) Fergusson College, University of Poona, Pune: 411 007, India

Selected Publications

  • Chavan S. P.; Garai S. ; Pawar K. P, "Asymmetric total synthesis of (-)-venlafaxine using an organocatalyst", Tetrahedron Letters., 54, 2137 - 2139 (2013).
  • Chavan S. P.; Harale K. R.; Pawar K. P, "A short synthesis of (2S, 3S)-3-hydroxypipecolic acid", Tetrahedron Letters., 54, 4851 - 4853 (2013).
  • Chavan S. P.; Lasonkar P. B, "One-pot migration-formylation of benzyl aryl ethers under Duff reaction condition", Tetrahedron Letters., 54, 4789 - 4792 (2013).
  • Chavan S. P.; Garai S. ; Dey C.; Gonnade R. G, "A highly stereocontrolled asymmetric total synthesis of epimer of (+)-7-deoxypancratistatin", Tetrahedron Letters., 54, 5562 - 5566 (2013).
  • Chavan S. P.; Lasonkar P.B.; Chavan P. N, "A novel and enantioselective synthesis of D-(+)-biotin via a Sharpless asymmetric dihydroxylation strategy", Tetrahedron Asymmetry., 24, 1473 - 1479 (2013).
  • Chavan S. P.; Lasonkar P.B, "pAaSimple Synthesis of the Novel Antihistaminic Drug Olopatadine Hydrochloride", Synthesis., 45, 3399 - 3403 (2013).
  • Chavan S. P.; Harale K. R.; Puranik V. G.; Gawade R. L, "Formal synthesis of (-)-stemoamide using a useful epimerization at C-8", Tetrahedron Letters., 53, 2647 - 2650 (2012).
  • Chavan S. P.; Harale K. R , "A very practical and selective method for PMB protection of alcohols", Tetrahedron Letters., 53, 4683 - 4686 (2012).
  • Chavan S. P.; Garai S. ; Kalkote U. R, "A highly diastereoselective total synthesis of (±)-Heritonin and (±)-Heritol", Tetrahedron., 68, 8509 - 8514 (2012).
  • Chavan S. P.; Khatod H. S, "Enantioselective synthesis of the essential oil and pheromonal component ar-himachalene by a chiral pool and chirality induction approach", Tetrahedron Asymmetry., 23, 1410 - 1415 (2012).
  • Chavan S. P.; Lasonkar P. B, "A chiral pool based approach to antipodes of alpha-cuparenone.", Tetrahedron Asymmetry., 23, 1496 - 1500 (2012).
  • Chavan S. P.; Garai S.; Dutta A. K.; Pal S, "Friedel–Crafts Acylation Reactions Using Esters", Eu. J. Org. Chem., 2012, 6841 - 6845 (2012), DOI:10.1002/ejoc.201201181.
  • Chavan S. P; Dumare N. B.; Harale K. R.; Kalkote U. R, "Asymmetric total synthesis of (2S,3S)-3-hydroxypipecolic acid", Tetrahedron Letters., 52, 404 - 406 (2011).
  • Panchgalle S. P.; Kunte S. S ; Chavan S. P. ; Kalkote U. R, "Exploration of L-proline catalyzed ?-aminoxylation of aldehyde towards (S)-guaifenesin related drug molecules", Syn. Commun., 41, 1938 - 1946 (2011).
  • Chavan S. P; Harale K. R.; Dumare N. B.; Kalkote U. R, "convenient formal synthesis of (2S,3S)-3-hydroxy pipecolic acid", Tetrahedron Asymmetry., 22, 587 - 590 (2011).
  • Chavan S. P; Dhawane A. N.; Kalkote U. R. , "Formal synthesis of (±)-camptothecin via tricyclic lactone as key synthon", Tetrahedron Letters., 51, 3099 - 3101 (2010).
  • Panchgalle S. P.; Bidwai H. B. ; Chavan S. P.; Kalkote U. R, "Organocatalytic asymmetric synthesis of (-)-delta-coniceine based on sequential proline-catalyzed asymmetric alpha-amination-HWE olefination", Tetrahedron Asymmetry., 21, 2399 - 2401 (2010).
  • Chavan S. P; Pathak A. B.; Pandey A.; Kalkote U. R, "Short and efficient synthesis of rubrolide E", Syn. Commun., 38, 3143 - 3149 (2008).
  • Chavan S. P; Thakkar M.; Kalkote U. R. And , "The first enantiospecific synthesis of (-)-heritol: absolute configuration determination", Tetrahedron Letters., 48, 643 - 646 (2007).
  • Chavan S. P; Thakkar M.; Jogdand G. F.; Kalkote U. R. And , "An enantiospecific synthesis of (+)-isoparvifolinone and (-)-parvifoline ", Tetrahedron Letters., 48, 535 - 537 (2007).
  • Chavan S. P; Dhawane A. N.; Kalkote U. R. And , "A facile total synthesis of (±)-?-cuparenone employing diallylation and RCM as key steps", Tetrahedron Letters., 48, 965 - 966 (2007).
  • Chavan S. P; Pathak A. B.; Dhawane A. N.; Kalkote U. R, "Total synthesis of Pulchellalactam via an RCM strategy ", Syn. Commun., 37, 1503 - 1510 (2007).
  • Chavan S. P; Pathak A. B.; Kalkote U. R. And , "A practical formal synthesis of camptothecin", Tetrahedron Letters., 48, 6561 - 6563 (2007).
  • Chavan S. P; Khobragade D. A.; Pathak A. B. And Kalkote U. R, "Convenient Formal Synthesis of (+)-Paroxetine", Syn. Commun., 37, 3143 - 3149 (2007).
  • Chavan S. P; Dhawane A. N.; Kalkote U. R, "An efficient and practical total synthesis of ?-cuparenone", Synthesis., 24, 3827 - 3830 (2007).
  • Chavan S. P; Pathak A. B.; Khobragade D. A. ; Thakkar M. T.; Kalkote U. R, "Practical Synthesis of (±)-Venlafaxine", Syn. Commun., 37, 3901 - 3906 (2007).
  • Chavan S. P; Thakkar M.; Jogdand G. F.; Kalkote U. R, "First Enantiospecific Synthesis of (?)-Parvifoline and (?)-Curcuquinone", J. Org. Chem., 71, 8986 - 8988 (2006), DOI:10.1021/jo061730d.
  • Chavan S. P; Sharma P.; Sivappa R..; Kalkote U. R, "A ring closing metathesis approach to the indole alkaloid mitralactonine ", Tetrahedron Letters., 47, 9301 - 9303 (2006).
  • Chavan And S P; Chittiboyina A. G.; Ravindranathan T.; Kamat S. K.; Kalkote U. R, "Diastereoselective Amidoalkylation of (3S,7aR)-6-Benzyl-7-hydroxy-3-phenyltetra- hydro-5H-imidazo[1,5-c][1,3]thiazol-5-one :? A Short and Highly Efficient Synthesis of (+)-Biotin", J. Org. Chem., 70, 1901 - 1903 (2005), DOI:10.1021/jo0488107.
  • Chavan S. P And ; Cherukupally P, "Stereoselective synthesis of (?)-microcarpalide", Tetrahedron Letters., 46, 1139 - 1941 (2005).
  • Chavan S. P ; Thakkar M.; Kharul R. K.; Pathak A. B.; Bhosekar G. V.; Bhadbhade M.; , "First enantiospecific synthesis of (+)-?-herbertenol ", Tetrahedron., 61, 3873 - 3879 (2005).
  • Panchgalle S. P. ; Kalkote U. R.; Niphadkar P. S.; Joshi P. N. ; Chavan S. P. ; Chaphekar G. M, "Sn-? molecular sieve catalysed Baeyer–Villiger oxidation in ionic liquid at room temperature", Green Chemistry., 6, 308 - 309 (2004), DOI:10.1039/B406077F.
  • Sudrik S. G.; Maddanimath T.; Chaki N. K.; Chavan S. P.; Chavan S. P.; Sonawane H. R.; Vijayamohanan K, "Evidence for the Involvement of Silver Nanoclusters during the Wolff Rearrangement of ?-Diazoketones", Org. Lett., 5, 2355 - 2358 (2003), DOI:10.1021/ol034747g.
  • Chavan S. P.; Sharma P.; Sivappa R.; Bhadbhade M. M.; Gonnade R. G. ; Kalkote U. R, "Enantioselective Synthesis of L-CCG-I", J. Org. Chem., 68, 6817 - 6819 (2003), DOI:10.1021/jo0345188.
  • Sudrik S. G.; Chavan S. P.; Chandrakumar K. R. S.; Pal S.; Date S. K.; Chavan S. P.; Sonawane H. R, "Microwave Specific Wolff Rearrangement of ?-Diazoketones and Its Relevance to the Nonthermal and Thermal Effect", J. Org. Chem., 67, 1574 - 1579 (2002), DOI:10.1021/jo010951a.
  • Chavan S. P ; Govande C. A, "Substrate to catalyst dependent conversion of ?,?-dihydroxyesters to butenolides and/or ?-ketoesters: synthesis of heritol, heritonin and mintlactones", Green Chemistry., 4, 194 - 195 (2002), DOI:10.1039/B109544G.
  • Chavan S. P.; Dantale S. W. ; Pasupathy K.; Tejwani R. B.; Kamat S. K.; Ravindranathan T. , "Facile conversion of oxathioacetals to carbonyl compounds", Green Chemistry., , 337 - 338 (2002), DOI:10.1039/B200754C.
  • Chavan S. P ; Tejwani R. B. ; Ravindranathan T, "A Switch of Reactivity Profile in Ionic Intramolecular Annulation Reactions:? A Short and Efficient Synthesis of d-(+)-Biotin", J. Org. Chem., 66, 6197 (2001), DOI:10.1021/jo015730j.
  • Ghorpade S. R And ; Kalkote U. R.; Bhide S. R.; Chavan S. P.; Ravindranathan T, "Efficient Synthesis of Optically Pure (4R,6S)-4-(tert-Butyldimethylsilyloxy)- 6-(hydroxymethyl)tetrahydropyran-2-one and Its Enantiomer", J. Org. Chem., 66, 6803 (2001), DOI:10.1021/jo015774s.
  • Kalkote U. R.; Ghorpade S. R.; Chavan S. P, "Simple, Efficient Chemoenzymatic Synthesis of (S)-5-(tert-Butyldimethylsilyloxy)-2-cyclohexenone and Enantiomeric Ketone Intermediates of 19-Nor-1?,25-dihydroxyvitamin D3", J. Org. Chem., 66, 8277 (2001), DOI:10.1021/jo016141g.
  • Chavan S. P ; Anand R; Pasupathy K; Rao B. S, "Catalytic acetylation of alcohols, phenols, thiols andamines with zeolite H-FER under solventless conditions", Green Chemistry., 3, 320 (2001), DOI:10.1039/B109093C.
  • Chavan S. P.; Rao Y.T.S, “ Ceric ammonium nitrate (CAN) mediated azidoalkylation of enol ethers and olefins.”, Tetrahedron Letters., 40, 5073 (1999).
  • Chavan S. P.; Patil S. S.; Ravindranathan T, “A simple synthesis of (±)-alpha-cuparenone.”, Tetrahedron., 55, 13417 (1999).
  • Chavan S. P.; Subbarao Y. T. ; Chittiboyina A. G , "Simple Synthesis of 2-Acetyl-5,8-dimethoxy-3,4-dihydronaphthalene: A Key Intermediate for the Synthesis of 4-Demethoxydaunomycinone", J. Chem. Res.(S)., , 380 (1999), DOI:10.1039/A901526D.
  • Sastry M.; Lala N.; Patil V.; Chavan S. P.; Chittiboyina A. G. , “ Optical Absorption Study of the Biotin-Avidin Interaction on colloidal Silver and Gold Particles.”, Langmuir., 14, 4138 (1998), DOI:10.1021/la9800755.
  • Chavan S. P.; Venkatraman M. S. , “A Practical and Efficient Synthesis of(±)Camptothecin", Tetrahedron Letters., 39, 6745 (1998).
  • Chavan S. P.; Dhondge V.D.; Patil S. S.; Rao Y. T. S, “ Enantiospecific Total synthesis of (+)-Laevigatin”, Tetrahedron Asymmetry., 8, 2517 (1997).
  • Chavan S.P.; Ravindranathan T.; Patil S.S.; Dantale S.W, “An Efficient Synthesis of a-Cuparenone.”, Tetrahedron Letters., 37, 2629 (1996).
  • Chavan S.P.; Ethiraj K. S, “Mg/MeOH Mediated Intramolecular Reductive Cyclisation of Activated Dienes.”, Tetrahedron Letters., 36, 2281 (1995).
  • Chavan S. P.; Zubaidha P. K.; Govande C.A.; Subba Rao, “ Novel Oxidative Conversion of b, g-Unsaturated Acids into Butenolides: Synthesis of Heritonin and Heritol.”, . J. Chem. Soc. Chem. Commun., , 1101 (1994), DOI:10.1039/C39940001101.
  • Chavan S. P.; Zubaidha P. K.; Dhondge V. D, “A Short and Efficient Synthesis of (-) Mintlactone and (+) Iso-Mintlactone.”, Tetrahedron., 49, 6429 (1993).
  • Chavan S. P.; Zubaidha P. K.; Ayyangar N. R. , “An Efficient entry into Butenolides Synthesis of (±) Mintlactone.”, Tetrahedron Letters., 33, 4605 (1992).
  • Zubaidha P. K.; Chavan S. P.; Racherla U. S.; Ayyangar N. R, “Synthesis of (±) Heritol.”, Tetrahedron., 47, 5759 (1991).
  • Gassman P. G.; Chavan S. P.; Fertel L. B, “The 2p+ 2p Cycloaddition of an allyl cation to (1Z, 3E)- Cycloalkadienes. Evidence for a Stepwise Process in the Ionic Diels - Alder Reaction.”, Tetrahedron Letters., 31, 6489 (1990).
  • Gassman P. G.; Chavan S. P. , “The ionic Diels–Alder reaction of 1-vinyl-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane. Retention of the ortho ester moiety through the use of the trioxabicyclo[2.2.2]octanyl protecting group”, J. Chem. Soc. Chem. Commun., , 837 - 839 (1989), DOI:10.1039/C39890000837.
  • Gassman P. ; Chavan S. P. , “The Low - Temperature , Ionic Diels - Alder Addition of Vinyl Orthoesters to 1,3 - Dienes.”, J. Org. Chem., 53, 2392 - 2394 (1988), DOI:10.1021/jo00245a058.
  • Gassman P. G.; Chavan S. P. , “Ethynyl ortho esters as precursors of propargyl cations: The low-temperature, ionic diels-alder addition of ethyl propiolate to 1,3-dienes via ethynyl ortho esters”, Tetrahedron Letters., 29, 3407 (1988).
  • Gassman P. G.; Singleton D. A.; Wilwerding J. A.; Chavan S. P. , “ Acrolein Acetals As Allyl Cation Precursors in the ionic Diels - Alder Reaction”, J. Am. Chem. Soc., 109, 2181 - 2182 (1987), DOI:10.1021/ja00241a046.
  • Rama Rao A. V.; Chavan S. P.; Sivadasan L, “ Synthesis of Lavendamycin”, Tetrahedron., 42, 5065 (1986).
  • Rama Rao A. V.; Chavan S. P.; Sivadasan L, “An approach Towards Synthesis of Lavendamycin”, Indian J. Chem., 23B, 496 (1984).

Research Interest

  • Total Synthesis of Bioactive Natural Products
  • Synthetic Methodologies
  • Asymmetric Synthesis
  • Process Development & scale-up

Contact Details

Dr. S. P. Chavan (Sci.-G)

Office:  Room No- 287,

Division of Organic Chemistry,

CSIR-National Chemical Laboratory,

Dr. Homi Bhabha Road,

Pune : 411 008 (MS), India

Phone:  +91 20 25902289

Fax: +91 20 25902629

E-mail:  sp.chavan@ncl.res.in