Chirality & Odour Perception
John C. Leffingwell, Ph.D.

The Dictyopterene B's

= The 1-((1E,3Z)-hexa-1,3-dienyl)-2-vinylcyclopropanes

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Photo by permission of M. Roudintska - Art & Parfum

c

(-)-(1R,2R)-Dictyopterene B - characteristic very intense, rather pleasant, "ocean smell"

= (-)-(1R,2R)-Hormosirene

= (-)-(1R,2R)-1-((1E,3Z)-hexa-1,3-dienyl)-2-vinylcyclopropane

Ref: Dieter Dorsch, Erika Kunz and Gunter Helmchen, Syntheses of dictyopterenene (hormosirene) and its enantiomer via asymmetric ScN' reactions, Tetrahedron Letters,Vol. 26, No.28, pp 3319-3322,1985; See also - Richard E. Moore, John A. Pettus Jr., James Mistysyn, Odoriferous C11 hydrocarbons from Hawaiian Dictyopteris, J. Org. Chem., 1974, 39 (15), pp 2201–2207; Richard E. Moore, Volatile compounds from marine algae Acc. Chem. Res., 1977, 10 (2), pp 40–47; Tadahiko Kajiwara, Yuuko Yamamoto, Yoshihiko Akakabe, Kenji Matsui, Hiroshi Shimizu, and Tesuo Kawai, Biomimetic Conversion of (3S)-(-)-Neodictyoprolenol to Optically Pure (1S,2R)-(-)-Dictyopterene B, Marine Algal Sex Pheromone, Z. Naturforsch. 58c, 109Ð112 (2003); Tadahiko Kajiwara. et al., Japanese Patent JP2003137819 (05/14/2003) (Note - Kajiwara. et al. in their publications incorrectly assigned the absolute configuration as 1S,2R).

c

 

(+)-(1S,2S)-Dictyopterene B - less intense and devoid of the rather pleasant, "ocean smell"

= (+)-(1S,2S)-Hormosirene

= (+)-(1S,2S)-1-((1E,3Z)-hexa-1,3-dienyl)-2-vinylcyclopropane

Ref: Dieter Dorsch, Erika Kunz and Gunter Helmchen, Syntheses of dictyopterenene (hormosirene) and its enantiomer via asymmetric ScN' reactions, Tetrahedron Letters,Vol. 26, No.28, pp 3319-3322,1985; See also - Richard E. Moore, John A. Pettus Jr., James Mistysyn, Odoriferous C11 hydrocarbons from Hawaiian Dictyopteris, J. Org. Chem., 1974, 39 (15), pp 2201–2207; Richard E. Moore, Volatile compounds from marine algae Acc. Chem. Res., 1977, 10 (2), pp 40–47; Tadahiko Kajiwara, Yuuko Yamamoto, Yoshihiko Akakabe, Kenji Matsui, Hiroshi Shimizu, and Tesuo Kawai, Biomimetic Conversion of (3S)-(-)-Neodictyoprolenol to Optically Pure (1S,2R)-(-)-Dictyopterene B, Marine Algal Sex Pheromone, Z. Naturforsch. 58c, 109Ð112 (2003); Tadahiko Kajiwara. et al., Japanese Patent JP2003137819 (05/14/2003) (Note - Kajiwara. et al. in their publications incorrectly assigned the absolute configuration as 1R,2S).

Cyclic Terpenoid Odorants

Bicyclic Terpenoid Odorants

Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

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