Second-generation synthesis of azadirachtin: a concise preparation of the propargylic mesylate fragment.

Abstract

A second bite of the apple: A new and highly efficient synthesis of the propargylic mesylate fragment of azadirachtin has been accomplished (see scheme; Bn = benzyl, Ms = methanesulfonyl, PMB = para-methoxybenzyl, TBDPS = tert-butyldiphenylsilyl). An enantioselective catalytic hetero Diels-Alder reaction sets up the stereocenter at C15, which then controls the installation of the remaining functionality in a total of only 17 steps.

• Authors: Alistair Boyer, Gemma E Veitch, Edith Beckmann, Steven V Ley
• Journal: Angewandte Chemie (International ed. in English) (Angew Chem Int Ed Engl) Vol. 48 Issue 7 Pg. 1317-20 ( 2009) ISSN: 1521-3773 [Electronic] Germany
• PMID: 19140148 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Lactones
• Limonins
• Mesylates
• azadirachtin

Topics

• Catalysis
• Lactones (chemistry)
• Limonins (chemical synthesis, chemistry)
• Mesylates (chemical synthesis, chemistry)
• Stereoisomerism