Asymmetric synthesis of a pheromone for Andrena haemorrhoa F from a chiral nitro alcohol obtained by the yeast reduction of a nitro ketone

✍ Scribed by Kaoru Nakamura; Takashi Kitayama; Yoshihiko Inoue; Atsuyoshi Ohno

• Book ID: 104204584
• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 703 KB
• Volume: 46
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)89061-x

✦ Synopsis

The o-position to the nitro group in 4-nitro-2-butanol or S-nitro-2-pentanol was acylated under DBU-catalysis after the hydroxy group was protected by a t-butyl dimethylsilyl group.

The prcscnt method has been applied to the asymmetric stercosclcctive synthesis of a pheromone for Andrsna haemorrkoa F, which has an interesting spiroacetal strucure. 1412 K. NAKAMURA ef al. Denitration of the resultant chiral 8-and y-hydroxy a'-keto nitro compounds gave the corresponding chiral y-and 6-hydroxy ketones, respectively. These substances are useful chiral building blocks for organic syntheses. Using