Formal Total Synthesis of Stevastelins B and B3

The formal total synthesis of stevastelins B and B3 (2 and 4, resp.) have been accomplished employing a highly enantiomerically controlled Lewis acid catalyzed non‐aldol approach to obtain the syn aldol product and temperature controlled hydroboration oxidation reaction to construct four consecutive...

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Bibliographic Details
Published in:Helvetica chimica acta 2014-05, Vol.97 (5), p.669-688
Main Authors: Singh Yadav, Jhillu, Sekhar Mandal, Satadru, Srihari, Pabbaraja
Format: Article
Language:English
Subjects:
Epoxidation
Macrolactamization
Macrolactonization
Non-aldol approach
Stevastelins B and B3
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Summary:The formal total synthesis of stevastelins B and B3 (2 and 4, resp.) have been accomplished employing a highly enantiomerically controlled Lewis acid catalyzed non‐aldol approach to obtain the syn aldol product and temperature controlled hydroboration oxidation reaction to construct four consecutive stereogenic centers. The other key reactions include Sharpless asymmetric epoxidation, macrolactonization, and macrolactamization towards building the core skeleton 2 and 4.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201300255