A convergent and stereochemically flexible synthetic route to spirastrellolide A has been explored.  The C1---�C15 carbon backbone was formed using the key steps of Jacobsen kinetic resolution followed by acid catalyzed tetrahydropyran formation.  The C18�C27 segment has been synthesized from L-tartaric acid by employing Lewis acid mediated alkyne addition and Brown crotylation strategies. Construction of the C32�C40 section has been accomplished.  Investigation of chlorohydrin formation entry into the C26�C33 chloride containing fragment is currently underway.

Studies toward the total synthesis of spirastrellolide a

239th National Meeting (2010)

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