Total Synthesis of Natural Enantiomers of Heliespirones A and C via the Diastereoselective Intramolecular Hosomi-Sakurai Reaction
β Scribed by Miyawaki, Akari; Kikuchi, Daisuke; Niki, Masu; Manabe, Yuki; Kanematsu, Makoto; Yokoe, Hiromasa; Yoshida, Masahiro; Shishido, Kozo
- Book ID
- 127233333
- Publisher
- American Chemical Society
- Year
- 2012
- Tongue
- English
- Weight
- 603 KB
- Volume
- 77
- Category
- Article
- ISSN
- 0022-3263
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## Abstract Natural Vincamine (**1**) has been synthesized in an enantioselective manner starting from the ethylpentenal **7**. In the key step a mixture of the diastereoisomeric racemates, **14** and **15**, was directly obtained from the silyl enol ether **11** and the dihydroβΞ²βcarboline **12**
The first total synthesis of(-)-benzomalvin A, which possesses 4(3H)-quinazolinone and 1,4-benzodiazepin-5-one moieties, was described. Both of 6-and 7-membered ring skeletons were efficiently constructed by the intramolecular aza-Wittig reactions as the key reactions. The enantiomeric excess of syn