Syntheses of xestodecalactone C and epi-sporostatin are described utilising Prins cyclisations, Mitsunobu reaction and intramolecular Friedel-Crafts acylation. The approach is convergent and highly stereoselective.
Stereoselective Total Synthesis of Xestodecalactone C
✍ Scribed by Karuturi Rajesh; Vangaru Suresh; Jondoss Jon Paul Selvam; Chitturi Bhujanga Rao; Yenamandra Venkateswarlu
- Book ID
- 102260261
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- German
- Weight
- 168 KB
- Volume
- 92
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
A simple and highly efficient stereoselective total synthesis of xestodecalactone C (IIb), a polyketide natural product, was achieved (Scheme 2). The synthesis involved Keck's asymmetric allylation, a iodine‐induced electrophilic cyclization, and an intramolecular Friedel–Crafts acylation as key steps.
📜 SIMILAR VOLUMES
## Abstract For Abstract see ChemInform Abstract in Full Text.
## Abstract A convergent and efficient total synthesis of stagonolide C (**1**), a phytotoxic metabolite, was achieved (__Schemes 2__ and __3__) The synthesis exploited the high configuration control in the __Prins__ cyclization along with alkene rearrangement and ring‐closing metathesis as key ste