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Studies Directed toward the Stereoselective Synthesis of Cytospolide E.

ABSTRACT: Our exhaustive effort toward the total synthesis of cytotoxic marine nonanolide cytospolide E has been detailed. To achieve this synthesis, we have explored both the ring-closing metathesis and lactonization-based macrocyclization strategies using a variety of precursors. Unfortunately, none of them provided the desired product. The ring-closing metathesis approach provided mainly the macrocycle with Z-olefin, whereas the macrolactonization strategy culminated in 8-epi-9-epi-cytospolide E following the regioselective formation of a 10-membered macrocycle over a 9-membered macrocycle.

SUBMITTER: Chatterjee S

PROVIDER: S-EPMC6641448 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Studies Directed toward the Stereoselective Synthesis of Cytospolide E.

Chatterjee Shamba S Kuilya Tapan Kumar TK Goswami Rajib Kumar RK

ACS omega 20180125 1

Our exhaustive effort toward the total synthesis of cytotoxic marine nonanolide cytospolide E has been detailed. To achieve this synthesis, we have explored both the ring-closing metathesis and lactonization-based macrocyclization strategies using a variety of precursors. Unfortunately, none of them provided the desired product. The ring-closing metathesis approach provided mainly the macrocycle with Z-olefin, whereas the macrolactonization strategy culminated in 8-<i>epi</i>-9-<i>epi</i>-cytosp ...[more]

PMID: 31457947

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