Diastereocontrol in the Synthesis of Models of Rings C and D of Phorbol: Directing Effect of an Ether Substituent on Lithium Carbenoid Mediated Cyclopropanation

✍ Scribed by Michael G. B. Drew; Laurence M. Harwood; Antonio J. Macías-Sánchez; Richard Scott; R. M. Thomas; Daniel Uguen

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 77 KB
• Volume: 40
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/1521-3773(20010618)40:12<2311::aid-anie2311>3.0.co;2-t

✦ Synopsis

The diastereocomplementarity of halo- and alkylcarbenes (paths a and b, respectively) was shown in the cyclopropanation reaction of 1. The conversion of 1 into 7,7-dimethylbicyclo[4.1.0]heptan-1,2-diols (±)-2 and (±)-3 represents an important transformation in a synthetic strategy towards phorbol derivatives. TBDMS=tert-butyldimethylsilyl.