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

doi:10.1021/ol500050p

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 journal › Letter

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 language	English
Pages (from-to)	1168-1171
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	4
Early online date	06 Feb 2014
DOIs	https://doi.org/10.1021/ol500050p
Publication status	Published - 2014

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10.1021/ol500050p

http://pubs.acs.org/doi/abs/10.1021/ol500050p

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@article{9ea4cbb9753043fea226b1938214ea8e,

title = "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",

abstract = "Abstract ImageHerein 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.",

author = "Hale, {Karl J.} and Maciej Maczka and Amarjit Kaur and Soraya Manaviazar and Mehrnoosh Ostovar and Milosz Grabski",

year = "2014",

doi = "10.1021/ol500050p",

language = "English",

volume = "16",

pages = " 1168--1171",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "4",

}

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

In: Organic Letters, Vol. 16, No. 4, 2014, p. 1168-1171.

Research output: Contribution to journal › Letter

TY - JOUR

T1 - 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

AU - Hale, Karl J.

AU - Maczka, Maciej

AU - Kaur, Amarjit

AU - Manaviazar, Soraya

AU - Ostovar, Mehrnoosh

AU - Grabski, Milosz

PY - 2014

Y1 - 2014

N2 - Abstract ImageHerein 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.

AB - Abstract ImageHerein 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.

U2 - 10.1021/ol500050p

DO - 10.1021/ol500050p

M3 - Letter

VL - 16

SP - 1168

EP - 1171

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 4

ER -