Total synthesis of (-)-reveromycin B.
[structure: see text] The total synthesis of the epidermal growth factor inhibitor reveromycin B (2) is described. A novel, convergent, and stereoselective reaction sequence was utilized to construct the 5,6-spiroketal system 10 which was converted into the natural product 2 by a 16-step sequence.
Cuzzupe
A N
AN
School of Chemistry, The University of Melbourne, Parkville, Victoria, Australia.
Hutton
C A
CA
Lilly
M J
MJ
Mann
R K
RK
Rizzacasa
M A
MA
Zammit
S C
SC
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D004815:Epidermal Growth Factor / Q000037:antagonists & inhibitors; D011714:Pyrans / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D011714:Pyrans; D013141:Spiro Compounds; C409389:reveromycin B; D004815:Epidermal Growth Factor