Development of methods suitable for natural product synthesis: The azadirachtin story
2005 ◽
Vol 77
(7)
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pp. 1115-1130
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Keyword(s):
Our synthesis work on the insect antifeedant azadirachtin is described. Particular emphasis is placed on the key coupling of a left-hand decalin fragment with a right-hand hydroxydihydrofuran acetal unit via a Claisen rearrangement reaction of an intermediate propargylic enol ether. New chemistry has been developed leading to control of an endo-selective intramolecular Diels–Alder reaction using silicon, which was essential for the construction of the appropriately functionalized decalin fragment. In order to install the five-ring hemiacetal of azadirachtin, we also developed a new ring contraction protocol via an intermediate six-ring cyano ester.
1986 ◽
Vol 19
(8)
◽
pp. 250-259
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Keyword(s):
Keyword(s):
2020 ◽
Vol 78
(3)
◽
pp. 204-212
Keyword(s):
1990 ◽
Vol 27
(1)
◽
pp. 47-69
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Keyword(s):