Synthesis of the C9-C25 Subunit of Spirastrellolide B

Soma Maitra, Mahipal Bodugam, Salim Javed, Paul R. Hanson

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The synthesis of the C9-C25 subunit of the marine natural product spirastrellolide B is reported. The key synthetic features included the union of the two key fragments 5 and 6 via a Suzuki-Miyaura coupling reaction and a late-stage, one-pot sequential deprotection/cascade Achmatowicz rearrangement-spiroketalization to install the key spirocyclic intermediate present in the C9-C25 fragment of spirastrellolide B. The synthesis of the C9-C16 fragment 6 was accomplished via a phosphate tether mediated ring-closing metathesis (RCM), a subsequent hydroboration-oxidation protocol, followed by other stereoselective transformations in a facile manner. The spirocyclic intermediate was further functionalized utilizing a Lindlar/NaBH4 reduction protocol to furnish the C9-C25 subunit 3.

Original languageEnglish (US)
Pages (from-to)3094-3097
Number of pages4
JournalOrganic Letters
Issue number13
StatePublished - Jul 1 2016

Bibliographical note

Funding Information:
Support for the NMR instrumentation was provided by NSF Grant Nos. 9512331, 9977422, and 0320648 and NIH Center Grant Nos. P20 GM103418, S10RR024664, and S10 OD016360.

Publisher Copyright:
© 2016 American Chemical Society.


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