Asymmetric Total Synthesis of (+)-Inthomycin C Via O-Directed Free Radical Alkyne Hydrostannation with Ph3SnH and Catalytic Et3B: Reinstatement of the Zeeck-Taylor (3R)-Structure for (+)-Inthomycin C

Karl J. Hale, Milosz Grabski, Soraya Manaviazar, Maciej Maczka

Research output: Contribution to journalLetter

27 Citations (Scopus)

Abstract

A new pathway to (+)-inthomycin C is reported that exploits an O-directed free radical hydrostannation reaction on (−)-12 and a Stille cross-coupling as key steps. Significantly, the latter process was effected on 19 where a gauche-pentane repulsive interaction could interfere. Our stereochemical studies on the alkynol (−)-12 and the enyne (+)-7 confirm that Ryu and Hatakeyama’s (3S)-stereochemical revision of (+)-inthomycin C is invalid and that Zeeck and Taylor’s original (3R)-stereostructure for (+)-inthomycin C is correct.
Original languageEnglish
Pages (from-to)1164-1167
Number of pages4
JournalOrganic Letters
Volume16
Issue number4
Early online date06 Feb 2014
DOIs
Publication statusPublished - 2014

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