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Biosci Biotechnol Biochem

Title:		"Protective group-free syntheses of (+/-)-frontalin, (+/-)-endo-brevicomin, (+/-)-exo-brevicomin, and (+/-)-3,4-dehydro-exo-brevicomin: racemic pheromones with a 6,8-dioxabicyclo[3.2.1]octane ring"
Author(s):		Mori K;
Address:		"Photosensitive Materials Research Center, Toyo Gosei Co., Ltd, Chiba, Japan. kjk-mori@arion.ocn.ne.jp"
Journal Title:		Biosci Biotechnol Biochem
Year:		2011
Volume:		20110520
Issue:		5
Page Number:		976 - 981
DOI:		10.1271/bbb.110071
ISSN/ISBN:		1347-6947 (Electronic) 0916-8451 (Linking)
Abstract:		"Protective group-free syntheses of four racemic pheromones with a 6,8-dioxabicyclo[3.2.1]octane ring were achieved in five or six steps from commercially available (+/-)-3-butyn-2-ol (6) and 2-alkenyl halides or 2-alken-1-ol by employing Lewis acid-catalyzed acetalization of delta, epsilon-epoxy ketones as the key reaction. (+/-)-Frontalin (1) was prepared in a 25% overall yield in five steps from methallyl chloride (5a), (+/-)-endo-brevicomin (2) was prepared in a 23% overall yield in five steps from (E)-2-pentenyl bromide (5b), and (+/-)-exo-brevicomin (3) and (+/-)-3,4-dehydro-exo-brevicomin (4) were both prepared in a 4% overall yield in six steps based on (Z)-2-penten-1-ol (12)"
Keywords:		"Bridged Bicyclo Compounds, Heterocyclic/chemical synthesis/chemistry Octanes/*chemistry Pheromones/*chemical synthesis/*chemistry Stereoisomerism;"
Notes:		"MedlineMori, Kenji eng England 2011/05/21 Biosci Biotechnol Biochem. 2011; 75(5):976-81. doi: 10.1271/bbb.110071. Epub 2011 May 20"