Synthesis of (+)-piclavines A1 and A2

Authors
McAlonan, H Potts, D Stevenson, PJ Thompson, N
Citation
H. Mcalonan et al., Synthesis of (+)-piclavines A1 and A2, TETRAHEDR L, 41(28), 2000, pp. 5411-5414
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
28
Year of publication
2000
Pages
5411 - 5414
Database
ISI
SICI code
0040-4039(20000708)41:28<5411:SO(AAA>2.0.ZU;2-A
Abstract
Piclavines AI and A2 have been synthesised for the first time. The route is short with the key step being the reaction of a bicyclic N-acyl iminium io n with 3-trimethysilyl-1-decene. This convergent strategy gave exclusively compounds in which the pendant decenyl group was axial, as a 6:1 mixture of E:Z-alkene diastereoisomers. Reduction of the lactam carbonyl group gave a 6:1 mixture of piclavines Al and A2, (C) 2000 Published by Elsevier Scienc e Ltd.