Total synthesis of (+)-fawcettimine.
نویسندگان
چکیده
The fawcettimine class of Lycopodium alkaloids consists of over 60 natural products. Typically, these tetracyclic compounds contain a single quaternary carbon center and are derived biosynthetically from the lycopodane core through an oxidative rearrangement reaction. In 1959, the first member of this class, fawcettimine (1), was isolated by Burnell in the Blue Mountain Range of Jamaica. Inubushi and co-workers later confirmed the structure by chemical correlation through X-ray crystallography. Heathcock and co-workers subse-
منابع مشابه
Enantiospecific formal total synthesis of (+)-fawcettimine.
The diastereospecific attack of the silyl enol ether on the activated cyclopropyl diester 27 generated the hydrindanone 28 with complete stereocontrol. Thermal decarbomethoxylation of 28 gave the monoester 29, a key intermediate in Heathcock's synthesis, thereby completing a formal total synthesis of (+)-fawcettimine 1. The analogous cyclization of 33, the diastereomer of 27, afforded the diast...
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The Lycopodium alkaloids are a family of structurally complex natural products, which have provoked long-term interests in their total syntheses because of their unique and fascinating architectures and potential biological activities. In particular, fawcettimine-type Lycopodium alkaloids, such as fawcettimine (1) and fawcettidine (2) (Scheme 1), have attracted broad attention from the syntheti...
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ورودعنوان ژورنال:
- Angewandte Chemie
دوره 46 40 شماره
صفحات -
تاریخ انتشار 2007