c
-dictyopterene_b.gif)
(-)-(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 22012207;
Richard E. Moore, Volatile compounds from marine
algae Acc. Chem. Res., 1977, 10 (2), pp
4047; 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).
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(+)-(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 22012207;
Richard E. Moore, Volatile compounds from marine
algae Acc. Chem. Res., 1977, 10 (2), pp
4047; 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).
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