Synthesis of the C1-C12 fragment of the tedanolides. Aldol-non-aldol aldol approach.
نویسندگان
چکیده
The combination of highly stereoselective non-aldol aldol and aldol processes allows the preparation of the completely protected C1-C12 fragment 2 of the novel macrocyclic cytotoxic agent tedanolide 1.
منابع مشابه
Anti aldol selectivity in a synthetic approach to the C1-C12 fragment of the tedanolides.
In a synthetic approach to the completely protected C1-C12 fragment of the macrocyclic cytotoxic agent tedanolide 1, we carried out the tin-catalyzed Mukaiyama aldol reaction between the 2,3-dialkoxypropanal 5 and the silyl enol ether 6 derived from the ketone 7, which gave, unexpectedly, the anti aldol isomer, rather than the expected syn isomer 4, as the major diastereomer formed.
متن کاملSynthesis of a fully functionalized protected C1-C11 fragment for the synthesis of the tedanolides.
[figure: see text] The use of several non-aldol aldol processes allows one to prepare a fully functionalized and completely protected C1-C11 fragment that should be useful for the total synthesis of the tedanolides.
متن کاملEfficient synthesis of the C(1)-C(11) fragment of the tedanolides. The nonaldol aldol process in synthesis.
[reaction: see text] The nonaldol aldol process developed in our laboratories has been applied to the synthesis of a C(1)-C(11) fragment 22 of the novel macrocyclic cytotoxic agents tedanolide and 13-deoxytedanolide 1 and 2. The commercially available hydroxy ester 7 was converted in 24 steps into compound 22 using two nonaldol aldol reactions.
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A synthesis of the C29-C51 fragment of spongistatin 1, containing the E and F rings, has been completed. The approach relies on four diastereoselective aldol additions and an asymmetric glycolate alkylation to establish eight of the eleven stereogenic centers. The intact chlorodiene side chain was appended by a Lewis acid catalyzed addition of an allylstannane to an epoxy enol ether.
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عنوان ژورنال:
- Organic letters
دوره 9 18 شماره
صفحات -
تاریخ انتشار 2007