Synthetic study of (+)-nootkatone from (-)-. beta.-pinene

…, M Miyashita, A Yoshikoshi

Index: Yanami, Tetsuji; Miyashita, Masaaki; Yoshikoshi, Akira Journal of Organic Chemistry, 1980 , vol. 45, # 4 p. 607 - 612

Full Text: HTML

Citation Number: 52

Abstract

A facile stereoselective synthesis of (+)-nootkatone (1) has been achieved starting with (+)- nopinone (2b). The key step was the conjugate addition of methallyltrimethylsilane (20b) to trans-3-ethylidenenopinone (16), which was obtainable from 2b on the cross condensation with acetaldehyde followed by acid treatment, giving an adduct with the desired stereochemistry, 24a, as the predominant product. Dione 23, obtained from the adduct on ...

~81%

An Efficient and Economic Asymmetric Synthesis of (+)-Nootka...

[Sauer, Anne M.; Crowe, William E.; Henderson, Gregg; Laine, Roger A. Organic Letters, 2009 , vol. 11, # 16 p. 3530 - 3533]

Biotransformation of aristolane-and 2, 3-secoaromadendrane-t...

[Furusawa, Mai; Hashimoto, Toshihiro; Noma, Yoshiaki; Asakawa, Yoshinori Chemical and Pharmaceutical Bulletin, 2006 , vol. 54, # 6 p. 861 - 868]

The total synthesis of (+)-nootkatone and (−)-7-epi-nootkato...

[Takagi,Y. et al. Tetrahedron, 1978 , vol. 34, p. 517 - 521]