Synthesis of the C(7)-C(22)-Sector of (+)-Acutiphycin Via O-Directed Double Free Radical Alkyne Hydrostannation with Ph3SnH/Et3B, Double I-Sn Exchange and Double Stille Coupling

Karl J. Hale, Maciej Maczka, Amarjit Kaur, Soraya Manaviazar, Mehrnoosh Ostovar, Milosz Grabski

Research output: Contribution to journalLetter

11 Citations (Scopus)

Abstract


Abstract Image

Herein a new double O-directed free radical hydrostannation reaction is reported on the structurally complex dialkyldiyne 11. Through our use of a conformation-restraining acetal to help prevent stereocenter-compromising 1,5-H-atom abstraction reactions by vinyl radical intermediates, the two vinylstannanes of 10 were concurrently constructed with high stereocontrol using Ph3SnH/Et3B/O2. Distannane 10 was thereafter elaborated into the bis-vinyl iodide 9 via O-silylation and double I–Sn exchange; double Stille coupling of 9, O-desilylation, and oxidation thereafter furnished 8.
Original languageEnglish
Pages (from-to) 1168-1171
Number of pages4
JournalOrganic Letters
Volume16
Issue number4
Early online date06 Feb 2014
DOIs
Publication statusPublished - 2014

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