Wittig ring contraction of the achiral 13-membered acetylenic ether 1 via treatment with lithio (R,R) or (S,S)-his-(1-phenylethyl)amide afforded the (RI-( +) or (S)-(-)-propargylic alcohol (+ J-2 or (-1-2, respectively, of >60% ee in 75% yield.
✦ LIBER ✦
Total synthesis of the germacranolide (±)-aristolactone via [2,3] wittig ring contraction
✍ Scribed by James A. Marshall; Jacques Lebreton; Bradley S. DeHoff; Todd M. Jenson
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 240 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
📜 SIMILAR VOLUMES
Enantioselective [2,3] wittig ring contr
✍
James A. Marshall; Jacques Lebreton
📂
Article
📅
1987
🏛
Elsevier Science
🌐
French
⚖ 221 KB
Synthesis of a possible kallolide a prec
✍
James A. Marshall; David J. Nelson
📂
Article
📅
1988
🏛
Elsevier Science
🌐
French
⚖ 269 KB
Synthesis of 6-hydroxycembrane precursor
✍
James A. Marshall; Edward D. Robinson; Jacques Lebreton
📂
Article
📅
1988
🏛
Elsevier Science
🌐
French
⚖ 279 KB
Total synthesis of (+)-eupomatilone 2 vi
✍
Yoshimi Hirokawa; Maria Kitamura; Chiharu Kato; Yuki Kurata; Naoyoshi Maezaki
📂
Article
📅
2011
🏛
Elsevier Science
🌐
French
⚖ 512 KB
Total synthesis of lycogarubin C utilizi
✍
Liangfeng Fu; Gordon W. Gribble
📂
Article
📅
2010
🏛
Elsevier Science
🌐
French
⚖ 320 KB
An efficient synthesis of lycogarubin C (3) was completed in seven steps from the known 1-(phenylsulfonyl)indole-3-carbaldehyde in 30% overall yield, via a Diels-Alder reaction between (Z)-1,2-di(1H-indol-3-yl)ethene 9b and dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (7), followed by a Kornfeld-Bog
The Synthesis of gem-Cyclopentyl Substit
✍
Stephen Challenger; Andrew Derrick; Terry V. Silk
📂
Article
📅
2003
🏛
John Wiley and Sons
⚖ 95 KB