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Formal Synthesis of (+)-Brefeldin A: Application of a Zinc-Mediated Ring Expansion Reaction.

✍ Scribed by Weimin Lin; Charles K. Zercher

Book ID
102010233
Publisher
John Wiley and Sons
Year
2007
Weight
23 KB
Volume
38
Category
Article
ISSN
0931-7597

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✦ Synopsis

Abstract

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A formal synthesis of (+)-brefeldin A
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A formal synthesis of (+)-brefeldin A has been achieved v/a stereoselective construction of hydroxycyclopentane skeleton possessing the requisite hydroxyheptenyl side chain. The highly advanced intermediate 2 has been synthesized from the known Weinreb amide in 19 % overall yield of 11 steps.

ChemInform Abstract: A Formal Synthesis
ChemInform Abstract: A Formal Synthesis of (+)-Brefeldin A.
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A Formal Synthesis of (+)-Brefeldin A. -An advanced synthetic intermediate for (+)-brefeldin A (IX) is efficiently synthesized from Weinreb amide (I). The procedure involves the highly stereoselective construction of the hydroxycyclopentane moiety via an oxabicycloheptanone unit. -(SUH,

ChemInform Abstract: Enantioconvergent F
ChemInform Abstract: Enantioconvergent Formal Synthesis of Brefeldin A via Sakai-Catalyzed Cyclization.
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Enantioconvergent Formal Synthesis of Brefeldin A via Sakai-Catalyzed Cyclization. -A formal total synthesis of the antitumor agent brefeldin A (XII) is presented by asymmetric synthesis of intermediate (XI). Key steps are the asymmetric Sakai cyclization of racemic pentenal (I) and the reductive a

Synthesis of Substituted Dibenzo[a,d]aze
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## Abstract Substituted dibenzoazepines 5 and 10 were synthesized in three steps by starting from acridine (6). The key step of the synthesis is a base‐mediated ring expansion reaction of the mesylates 1.