Total Synthesis of (-)-(7S,10R)-Calamenene and (-)-(7S,10R)-2-Hydroxycalamenene by Use of a Ring-Closing Metathesis Reaction. A Comparison of the cis- and trans-Isomers

doi:10.3390/70700517

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Molecules 2002, 7(7), 517-527; doi:10.3390/70700517

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Total Synthesis of (-)-(7S,10R)-Calamenene and (-)-(7S,10R)-2-Hydroxycalamenene by Use of a Ring-Closing Metathesis Reaction. A Comparison of the cis- and trans-Isomers

Katsuyuki Nakashima, Masashi Imoto, Masakazu Sono, Motoo Tori* , Fumihiro Nagashima and Yoshinori Asakawa

Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, 770-8514, Japan

* Author to whom correspondence should be addressed.

Received: 2 May 2002; in revised form: 1 July 2002 / Accepted: 8 July 2002 / Published: 31 July 2002

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Abstract: The title compounds have been synthesized starting from l-menthone by application of a ring-closing metathesis reaction to confirm their reported absolute and relative stereochemistry. Comparisons of the NMR spectra and specific rotations are also discussed.

Keywords: Calamenene; hydroxycalamenene; ring closing metathesis; absolute configuration; sesquiterpene

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MDPI and ACS Style

Nakashima, K.; Imoto, M.; Sono, M.; Tori, M.; Nagashima, F.; Asakawa, Y. Total Synthesis of (-)-(7S,10R)-Calamenene and (-)-(7S,10R)-2-Hydroxycalamenene by Use of a Ring-Closing Metathesis Reaction. A Comparison of the cis- and trans-Isomers. Molecules 2002, 7, 517-527.

AMA Style

Nakashima K, Imoto M, Sono M, Tori M, Nagashima F, Asakawa Y. Total Synthesis of (-)-(7S,10R)-Calamenene and (-)-(7S,10R)-2-Hydroxycalamenene by Use of a Ring-Closing Metathesis Reaction. A Comparison of the cis- and trans-Isomers. Molecules. 2002; 7(7):517-527.

Chicago/Turabian Style

Nakashima, Katsuyuki; Imoto, Masashi; Sono, Masakazu; Tori, Motoo; Nagashima, Fumihiro; Asakawa, Yoshinori. 2002. "Total Synthesis of (-)-(7S,10R)-Calamenene and (-)-(7S,10R)-2-Hydroxycalamenene by Use of a Ring-Closing Metathesis Reaction. A Comparison of the cis- and trans-Isomers." Molecules 7, no. 7: 517-527.

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