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

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, 2.0 M in cyclohexane
Sigma-Aldrich
n-Butyllithium solution, 1.6 M in hexanes
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