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Studies on the asymmetric total synthesis of trichothecenes. Stereoselective construction of the c-ring fragment

✍ Scribed by Duy H. Hua; S. Venkataraman

Publisher: Elsevier Science
Year: 1985
Tongue: French
Weight: 262 KB
Volume: 26
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)89245-x

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✦ Synopsis

A stereoselective construction of the C-ring fragment of trichothecenes from readily available 4-cumyloxy-2-cyclopentenol in 12 steps (24% overall yield) is described. We have recently described an asymmetric synthesis based on the reaction of enones with chiral sulfinylallyl anions.' The utilization of this Michael-type addition reaction in the asymmetric synthesis of trichothecene mycotoxins 2 is being developed. In this communication we describe a stereoselective construction of the C-ring fragment (1) 394 of trichothecenes from the readily available 4-cumyloxy-2-cyclopenten-l-01 (z).5

Oxidation of alcohol 2 with 1.5 equiv. of pyridinium chlorochromate 6 and 3A molecular sieves in CH2C12 at r.t. for 1 h provided enone 3_ in 95% yield. Treatment of enone 2 with 1.1 equiv. of CH3Li in THF (40 mL/g of 2) at -30°C for 1 h gave alcohol 5 7. in 86% yield and isomer

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