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

被引：37

作者：

Hale, Karl J. ^{[1
]}

Grabski, Milosz

Manaviazar, Soraya

Maczka, Maciej

机构：

[1] Queens Univ Belfast, Sch Chem & Chem Engn, Belfast BT9 5AG, Antrim, North Ireland

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 04期

关键词：

ENANTIOSELECTIVE SYNTHESIS; TERMINAL ALKYNES; ALDEHYDES; ION; DIHYDROXYLATION; PHTHOXAZOLIN; ALCOHOLS; NMR;

D O I：

10.1021/ol5000499

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1164 / 1167

页数：4

共 25 条

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