Open AccessSynthesis of the C9–C25 Subunit of Spirastrellolide B
Author(s) -
Soma Maitra,
Bodugam Mahipal,
Salim Javed,
Paul R. Hanson
Publication year - 2016
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.6b01248
Subject(s) - chemistry , hydroboration , stereochemistry , metathesis , stereoselectivity , protein subunit , natural product , salt metathesis reaction , dig , combinatorial chemistry , catalysis , organic chemistry , polymerization , biochemistry , computer security , computer science , gene , polymer
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.