Unexpected ring C enlargement of the aspidospermane skeleton

Authors
Lewin, G Schaeffer, C Hocquemiller, R
Citation
G. Lewin et al., Unexpected ring C enlargement of the aspidospermane skeleton, TETRAHEDR L, 42(51), 2001, pp. 8985-8987
Citations number
5
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
51
Year of publication
2001
Pages
8985 - 8987
Database
ISI
SICI code
0040-4039(200112)42:51<8985:URCEOT>2.0.ZU;2-R
Abstract
Treatment of (-)-16-chloro-1-dehydro-5-methoxy-vineadifformine 4 with Ac2O- pyridine led to the rearranged compound 6 through an unexpected ring C expa nsion. Upon reaction with dimethyl acetylenedicarboxylate. 4 provided the [ 2+2] cycloaddition derivative 9 but did not undergo the ring C enlargement. (C) 2001 Elsevier Science Ltd. All rights reserved.