Total synthesis of (+/-)-nakamurol-A and its 13-epimer: tentative assignment of the C-13 relative configuration

Authors
Bonjoch, J Cuesta, J Diaz, S Gonzalez, A
Citation
J. Bonjoch et al., Total synthesis of (+/-)-nakamurol-A and its 13-epimer: tentative assignment of the C-13 relative configuration, TETRAHEDR L, 41(30), 2000, pp. 5669-5672
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
30
Year of publication
2000
Pages
5669 - 5672
Database
ISI
SICI code
0040-4039(20000722)41:30<5669:TSO(AI>2.0.ZU;2-W
Abstract
A general approach to the structure of thelepogan-type diterpenoids has bee n developed and its application to the first total synthesis of (+/-)-nakam urol-A is described. The key steps involve: (i) a diastereoselective dimeth ylzine addition to an endocyclic enone followed by enolate trapping; (ii) a Sakurai allylation of an exocyclic enone; and (iii) a Wacker chemoselectiv e oxidation. The H-1 NMR data for the synthetic nakamurol-A and its C-13 ep imer allow a tentative assignment of the relative configuration at C-13 of the natural product. (C) 2000 Elsevier Science Ltd. All rights reserved.