Abstract
An 11-step approach to tricyclic compound 42, which contains the alkaloidal nucleus of the marine natural product sarain A (1), has been developed. Pivotal steps in the construction of 42 include stereospecific intramolecular dipolar [3 + 2]-cycloaddition of an azomethine ylide generated from aziridine 27 to afford bicyclic lactam 28 and a novel intramolecular allylsilane/N-tosyliminium ion cyclication of 41 to produce the tricycle.
Original language | English (US) |
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Pages (from-to) | 4945-4951 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 58 |
Issue number | 18 |
DOIs | |
State | Published - Jan 1 1993 |
All Science Journal Classification (ASJC) codes
- Organic Chemistry