jo9804700_si_001.pdf (1.21 MB)
Synthesis of (±)-Allocyathin B2 and (+)-Erinacine A
journal contribution
posted on 1998-06-12, 00:00 authored by Barry B. Snider, Nha Huu Vo, Steven V. O'Neil(±)-Allocyathin B2 (2) and (+)-erinacine A (4), the 1-β-d-xyloside of (+)-allocyathin B2, the first
cyathin diterpenes to be prepared, have been synthesized using a carbonyl ene reaction of 14a to
construct an appropriately functionalized seven-membered ring and palladium-catalyzed carbonylation of dienyl triflates 10 and 39 as key steps. The entire cyathin carbon skeleton is constructed
in seven steps, and allocyathin B2 is synthesized in only 17 steps (>5% overall yield) from readily
available enone 9.