Total Synthesis of (+/-)-Cylindricine C

A concise synthesis of (+/-)-cylindricine C and its C(13)-epimer is described. Starting from 1-octyne, cylindricine C and 13-epi-cylindricine C were prepared in 11% and 15% yields, respectively. The synthesis involves the preparation of the central tricyclic moiety via a radical alpha-iodoketone carboazidationibis-reductive amination sequence. Inversion of the stereochemistry at C(13) and C(5) was efficiently achieved on late stage intermediates.


Published in:
Organic Letters, 13, 4774-4777
Year:
2011
Keywords:
Laboratories:




 Record created 2011-12-16, last modified 2018-01-28


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)