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 | |
| Publication status | Published - 2014 |
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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 -