- REGIOSPECIFIC SYNTHESIS OF DIOXABICYCLOOCTANES CONTAINING A TERMINAL PRENYL SIDECHAIN
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A Wittig reaction employing the ylide generated from isopropyl triphenylphosphonium bromide with THP-protected aldol intermediate 8 constitutes the key step in a regiospecific synthesis of olefin 1 in the total synthesis of zoapatanol analogue 2a.
- Hajos, Zoltan G.,Wachter, Michael P.,Adams, Richard E.,Werblood, Harvey M.
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p. 2891 - 2896
(2007/10/02)
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- Synthesis and Antifertility Activity of Zoapatanol Analogues
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The synthesis of and guinea pig contragestational screening data for several oxepane and 3,8-dioxabicyclooctane analogues of zoapatanol (1) are described and their structure-activity relationships discussed.Conversion of the 5-keto group on the nonenyl side chain of 1 into a hydroxyl function enhanced the potency.Further significant enhancement in the potency was realized with the transformation of several oxepanes into the 3,8-dioxabicyclooctane-1-acetic acid derivatives.Detailed, comparative contragestational evaluation of the three most potent compounds 9, 33, and 37 is presented, which led to the selection of 33 (ORF 13811) for further biological evaluation.
- Kanojia, Ramesh M.,Chin, Eva,Smith, Carol,Chen, Robert,Rowand, Deborah,et al.
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p. 796 - 803
(2007/10/02)
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- (1RS,4SR,5RS)-4-(5-Hydroxy-4,8-dimethyl-7-nonen-1-yl)-4-methyl-3,8-dioxabicyclooctane-1-acetic Acid from Geraniol
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(E)-Geraniol (4) has been converted via 13 steps involving epoxidations, hydrolytic epoxide ring opening, and two ring closures to the key intermediate 3,8-dioxabicyclooctane alcohol 10 having stereochemical integrity at all three centers of asymmetry.Extension of the three-carbon side chain of 10 and attachment of the acetic acid side chain at C-1 in nine steps completed the geraniol-based total synthesis of the zoapatanol related bicyclic acid 3.The total synthesis of 3 from the ketal-ketone 5 has also been described.
- Hajos, Zoltan G.,Wachter, Michael P.,Werblood, Harvey M.,Adams, Richard E.
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p. 2600 - 2608
(2007/10/02)
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- Chemical compounds and processes
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Chemical compounds having a substituted oxepane ring and methods of preparing such compounds are described. The compounds are active as utero-evacuant agents.
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- Oxepanes
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Chemical compounds having a substituted oxepane ring and methods of preparing such compounds are described. The compounds are active as utero-evacuant agents.
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