☆ 4.8 Article

Synthetic Studies on Aculeximycin: Synthesis of C24-C40 Segment by Kobayashi Aldolization and Epoxide Rearrangements

ORGANIC LETTERS (2015)

期刊

ORGANIC LETTERS

卷 17, 期 9, 页码 2274-2277

出版社

AMER CHEMICAL SOC

DOI: 10.1021/acs.orglett.5b00965

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类别

Chemistry, Organic

资金

NOVARTIS Foundation (Japan) for the Promotion of Science
Kurata Memorial Hitachi Science and Technology Foundation
Naito Foundation
GCOE program Center for Practical Chemical Wisdom
Scientific Research on Innovative Areas of The Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan [24102531]
Supporting Strategic Research Platform for Fusion Biotechnology based on Biology, Chemistry, and Informatics Project to Form the Strategic Research Platforms for Private University
MEXT, Japan
Grants-in-Aid for Scientific Research [24102531] Funding Source: KAKEN

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摘要

Stereoselective synthesis of the C24-C40 segment of aculeximycin has been achieved by using the Kobayashi aldol reactions and epoxy-opening rearrangement reactions. The C33-C40 segment was synthesized by the Kobayashi aldol reaction followed by epoxidation and Jung rearrangement of epoxide 9, while the C25-C32 segment was constructed by the Kobayashi aldol reaction followed by epoxidation and the epoxy-opening rearrangement reaction of epoxide 13. These segments were connected by the aldol reaction and the sequential dehydration, reduction, and conversion of ethyl ester to ethyl ketone to give the C24-C40 segment 1. All stereogenic centers were constructed by substrate-controlled stereoselective reactions.

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