Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Download PDF
Synlett
DOI: 10.1055/a-2735-9451
DOI: 10.1055/a-2735-9451
Letter
Published as part of the Special Issue dedicated to Prof. S. Chandrasekaran on his
80th birthday
Biomimetic Total Synthesis of Homodimeric Diels–Alder Adduct Thamnosin
Authors
Supported by: Science and Engineering Research Board (SERB) CRG/2022/002967
Dedication
This manuscript is dedicated to Prof. S. Chandrasekaran on his 80th birthday.
Abstract
Thamnosin is a homodimeric Diels–Alder adduct. Model studies revealed that, with fine-tuning of the reaction conditions, two different modes of diene dimerization could be achieved. This strategy was successfully applied to the total synthesis of thamnosin.
Keywords
Homodimeric Diels–Alder - Dimerization - Biomimetic synthesis - Antifungal agents - AntimalarialPublication History
Received: 08 September 2025
Accepted after revision: 17 October 2025
Article published online:
21 November 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1 Radcliffe CB, Short WF. J Soc Chem Ind 1928; 47: 324T
- 2 Briggs LH, Cambie RC. Tetrahedron 1958; 2: 256
- 3 Brown KL, Burfitt AIR, Cambie RC, Hall D, Mathai KP. Aust J Chem 1975; 28: 1327-1337
- 4 Dreyer DL. Tetrahedron 1966; 22: 2923
- 5a Kearney TH, Peebles RH. Arizona Flora. Berkeley and Los Angeles. California: University of California Press; 1960: 494
- 5b Benson L, Darrow RA. A Manual of Southwestern Desert Trees and Shrubs. Tucson, Arizona: University of Arizona; 1945: 210
- 7 Kutney JP, David TI, Dreyer L. J Am Chem Soc 1968; 90: 813
- 8 Sharma PN, Shoeb A, Kapil R, Popli SP. Phytochemistry 1980; 19: 1258
- 9 Dey BB, Pillay PP, David JC, Rajamanikam N. Indian J Med Res 1935; 22: 765
- 10 Dhawan BN, Patnaik GK, Rastogi RP, Singhi KK, Tandon JS. Indian J Exp Biol 1977; 15: 208
- 11 Makangara JJ, Henry L, Jonker SA, Nkunya MHH. Phytochemistry 2004; 65: 227
- 12 Vougogiannopoulou K, Fokialakis N, Aligiannis N, Cantrell C, Skaltsounis A-L. Org Lett 2010; 12: 1908
- 13 Reisch J, Herath HMTB, Kumar NS. Liebigs Ann Chem 1990; 931
- 14 Concannon SM, Ramachandran VN, Smyth WF. Tetrahedron Lett 2000; 41: 9909
- 15 Mulzer J, Kühl U, Huttner G, Evertz K. Chem Ber 1988; 121: 2231
- 16 Dethe DH, Erande RD, Dherange BD. Org Lett 2014; 16: 2764
- 17 CCDC 1533565 contains supplementary crystallographic data for compound 21b
- 18a Nicolaou KC, Snyder SA, Montagnon T, Vassilikogiannakis G. Angew Chem Int Ed 2002; 41: 1668
- 18b Reymond S, Cossy J. Chem Rev 2008; 108: 5359
- 18c Paddon-Row MN, Sherburn MS. Chem Commun 2012; 48: 832
- 19 Pereira S, Srebnik M. Organometallics 1996; 14: 3127
- 20 Kimura M, Futamata M, Mukai R, Tamaru Y. J Am Chem Soc 2005; 127: 4592