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Merck

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
RESUMEN

[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.