Elucidation of Racemization Process of Azaspirene Skeleton in Neutral Aqueous Media

Azaspirene and related congeners, which possess various biological activities, have a unique spirocyclic core structure. However, there are few studies on the chemical properties of (−)-azaspirene, despite the fact that it may provide important insights into unveiling the biosynthetic pathway. Here,...

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Published inJournal of organic chemistry Vol. 83; no. 23; pp. 14457 - 14464
Main Authors Hirasawa, Shun, Mukai, Ken, Sakai, Shinnosuke, Wakamori, Shinnosuke, Hasegawa, Takahiro, Souma, Kazunori, Kanomata, Nobuhiro, Ogawa, Narihito, Aizawa, Mamoru, Emoto, Makoto
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.12.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PSEUROTIN-A
ABSOLUTE-CONFIGURATION
SYNERAZOL
BIOSYNTHESIS
MARINE-DERIVED ASPERGILLUS
ANGIOGENESIS INHIBITOR
ASYMMETRIC TOTAL-SYNTHESIS
METABOLITE
ANHYDRIDE
FUMIGATUS
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Summary:Azaspirene and related congeners, which possess various biological activities, have a unique spirocyclic core structure. However, there are few studies on the chemical properties of (−)-azaspirene, despite the fact that it may provide important insights into unveiling the biosynthetic pathway. Here, we report a nine-step chemical synthesis of an azaspirene analogue with a new finding that the natural (−)-azaspirene skeleton easily racemizes in neutral aqueous media.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02223