Stereocontrolled synthesis of the diene and triene macrolactones of oximidines I and II: Organometallic coupling versus standard macrolactonization

Authors
Coleman, RS Garg, R
Citation
Rs. Coleman et R. Garg, Stereocontrolled synthesis of the diene and triene macrolactones of oximidines I and II: Organometallic coupling versus standard macrolactonization, ORG LETT, 3(22), 2001, pp. 3487-3490
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
22
Year of publication
2001
Pages
3487 - 3490
Database
ISI
SICI code
1523-7060(20011101)3:22<3487:SSOTDA>2.0.ZU;2-Z
Abstract
[GRAPHICS] Stereocontrolled construction of the 12-membered diene and triene lactones 1, 2, and 3, characteristic of the antitumor agent oximidines I and II, are reported and were based on an intramolecular Castro-Stephens coupling for the construction of a cyclic enyne or dienyne followed by stereoselective r eduction of the cyclic alkyne for introduction of the cis-olefin of the tar gets. A comparison of the effectiveness of this protocol is made with stand ard macrolactonization.