Development of an approach to the synthesis of the ABC ring system of Hemibrevetoxin B.
An efficient approach for the synthesis of a model of the ABC ring system of Hemibrevetoxin B is described. Key features include a ring expansion to yield the ring C oxepane, the reduction of a 2-furyl ketone with high levels of 1,3-stereocontrol, and an Achmatowicz oxidative ring expansion to yield the ring A tetrahydropyran. All seven stereogenic centers present in the model compound were controlled with high levels (>98:<2) of diastereoselectivity.
Crawford
Claire
C
School of Chemistry, University of Leeds, Leeds LS2 9JT, UK.
Nelson
Adam
A
Patel
Ian
I
D000818:Animals; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D011161:Porifera; D013237:Stereoisomerism
D006576:Heterocyclic Compounds, 4 or More Rings; C409729:hemibrevetoxin B