Stereocontrolled synthesis of serricornin

Details Stereocontrolled synthesis of serricornin Stereocontrolled synthesis of serricornin

1997-09-04

1998-10-06

McKane, Joseph

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

5689095, C07C 4500

Patent

active

058178821

ABSTRACT:
Serricornin, the attractant pheromone of the cigarette beetle, is synthesized in high enantiomeric and diastereomeric purity via a series of reactions of asymmetric 2-(1-haloalkyl)-1,3,2-dioxaborolanes with Grignard reagents, which lead to the key intermediate the carbon-carbon double bond of and sodium periodate yields serricornin.

REFERENCES:
patent: 4525309 (1985-06-01), Matteson et al.
Kuwahara, Y. et al., "Chemical Studies on the Anobiidae: Sex Pheromone of the Drugstore Beetle, Stegobium Paniceum (L.) (Coleoptera)," Tetrahedron, 34:1769-1774 (1978).
Mori, M. et al., "Inhibitory Action of (4S,6S,7R)-Isomer to Pheromonal Activity of Serricornin, (4S,6S,7S)-7-Hydroxy-4,6-Dimethyl-3-Nonanone," J. Chem. Ecol., 12(1):83-89 (1986).
Mori, K. and Watanabe, H., "A New Synthesis of Serricornin Cigarette Beetle," Tetrahedron, 41(16):3423-3428 (1985).
Tripathy, P.B. and Matteson, D.S., "Asymmetric Synthesis of the Four Stereoisomers of 4-Methyl-3-heptanol via Boronic Esters: Sequential Double Stereodifferentiation Leads to Very High Purity," Synthesis, 3:200-206 (1990).
Sadhu, K.M. and Matteson, D.S., "(Chloromethyl)lithium: Efficient Generation and Capture by Boronic Esters and a Simple Preparation of Dilsopropyl (Chloromethyl)boronate," Organometallics, 4:1687-1689 (1985).
Matteson, D.S. and Man, H.-W., "Enantioselective Capture and Retroracemization of (1-Bromoalkyl)boronic Esters by an N-Propanoyloxazolidinone Enolate and Iodide Ion,"J. Org. Chem., 59:5734-5741 (1994).
Pappo, R. et al., "Osmium Tetroxide-Catalyzed Periodate Oxidation of Olefinic Bonds," J. Org. Chem., 21:478-479 (1956).
Matteson et al., J. Am. Chem. Soc., 108:812-819, 1986.

Affiliated with

Also associated with

Rating

Stereocontrolled synthesis of serricornin does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Stereocontrolled synthesis of serricornin, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Stereocontrolled synthesis of serricornin will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-79949