Synthesis of Sominone and Its Derivatives Based on an RCM Strategy: Discovery of A Novel Anti-Alzheimer’s Disease Medicine Candidate “Denosomin”

Synthesis of sominone was achieved starting from dehydroepiandrosterone on the basis of an RCM strategy for the construction of a δ-lactone side chain. This synthetic protocol was applied for the synthesis of several analogous derivatives including 1-deoxy-24-norsominone (denosomin), which was revea...

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Bibliographic Details
Published in:Organic letters 2009-09, Vol.11 (17), p.3970-3973
Main Authors: Matsuya, Yuji, Yamakawa, Yu-ichiro, Tohda, Chihiro, Teshigawara, Kiyoshi, Yamada, Masashi, Nemoto, Hideo
Format: Article
Language:English
Subjects:
Alzheimer Disease - drug therapy
Dehydroepiandrosterone - analogs & derivatives
Dehydroepiandrosterone - chemical synthesis
Dehydroepiandrosterone - chemistry
Drug Design
Molecular Structure
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Summary:Synthesis of sominone was achieved starting from dehydroepiandrosterone on the basis of an RCM strategy for the construction of a δ-lactone side chain. This synthetic protocol was applied for the synthesis of several analogous derivatives including 1-deoxy-24-norsominone (denosomin), which was revealed to exhibit notable bioactivities for new antidementia chemotherapy, exceeding the original natural compound sominone.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol901553w