10.1021/ol051175m.s004
Amit K. Mandal
Amit K.
Mandal
John S. Schneekloth,
John S.
Schneekloth,
Craig M. Crews
Craig M.
Crews
Stereoselective Assembly of a 1,3-Diene
via Coupling between an Allenic Acetate
and a (<i>B</i>)-Alkylborane: Synthetic
Studies on Amphidinolide B1
American Chemical Society
2005
amphidinolide B 1
diene
Allenic Acetate
C 21
C 16 stereochemistry
Stereoselective Assembly
novel stereoselective method
heteroene reaction
Amphidinolide B 1
C 9 configuration
allylation reaction
allylic alkylation
allenic acetate
C 25 stereogenic centers
2005-08-18 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Stereoselective_Assembly_of_a_1_3_Diene_via_Coupling_between_an_Allenic_Acetate_and_a_i_B_i_Alkylborane_Synthetic_Studies_on_Amphidinolide_B1/3272443
The preparation of three fragments for the total synthesis of amphidinolide B1 has been described. The C16 stereochemistry was set by
asymmetric allylic alkylation. C21 and C25 stereogenic centers were set by an enantioselective/diastereoselective double allylation reaction.
The C9 configuration was set by an asymmetric heteroene reaction. A differentially substituted stereodefined 1,3-diene iodide was synthesized
by iodide-mediated S<sub>N</sub>2‘ reaction. A novel stereoselective method to assemble a 1,3-diene by coupling an allenic acetate and (<i>B</i>)-alkylborane
is also reported.