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New, abridged pathway to Masamune's "southern hemisphere" intermediate for the total synthesis of bryostatin 7.

Organic letters (2003-02-14)
Karl J Hale, Mark Frigerio, Soraya Manaviazar
ABSTRACT

[reaction: see text] The "Southern Hemisphere" intermediate 2, used by Masamune and co-workers for their asymmetric total synthesis of bryostatin 7 (1), has been synthesized from (E)-1,4-hexadiene (11) by a 24-step pathway that has a longest linear sequence of only 20 steps. This is the shortest synthesis of 2 so far recorded, and moreover, it is fully stereocontrolled.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
n-Butyllithium solution, 2.5 M in hexanes
Sigma-Aldrich
n-Butyllithium solution, 11.0 M in hexanes
Sigma-Aldrich
n-Butyllithium solution, 2.7 M in heptane
Sigma-Aldrich
n-Butyllithium solution, 2.0 M in cyclohexane
Sigma-Aldrich
n-Butyllithium solution, 1.6 M in hexanes
Sigma-Aldrich
n-Butyllithium solution, 1.4 M in toluene