- PREHISPANOLONE, A LABDANE DITERPENE FROM LEONURUS HETEROPHYLLUS
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A new labdane diterpene, prehispanolone, has been isolated from Leonurus heterophyllus.Its structure, 9α,13R;15,16-diepoxylabdan-14-en-7-one, was established by spectroscopic means as well as by examination of its derivatives.
- Hon, Po-Ming,Lee, Chi-Ming,Shang, Hong-Sheng,Cui, Yu-Xin,Wong, Henry N. C.,Chang, Hson-Mou
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- Total synthesis of (-)-hispanolone and an improved approach towards prehispanolone
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On the basis of the recently reported construction of (±)-hispanolone (2), the enantiomerically pure form of (-),2, employed in our partial synthesis of the specific platelet activating factor receptor antagonist prehispanolone (3), was prepared from (S)-
- Cheung, Wing Shun,Wong, Henry N. C.
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p. 11001 - 11016
(2007/10/03)
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- Total syntheses of naturally occurring molecules possessing 1,7- dioxaspiro[4.4]nonane skeletons
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The syntheses of several naturally occurring molecules, namely prehispanolone, sphydrofuran, secosyrins, and syringolides are reviewed. Interestingly, these compounds are all structurally related, possessing a 1,7-dioxaspiro[4.4]nonane framework. The pivotal step in these synthetic endeavors involves the peracid oxidation of substituted 2- trimethylsilylfurans to but-2-en-4-olides. A subsequent intramolecular Michael addition procedure was also essential in the construction of the spiro skeleton. Two significant issues concerning regioselectivity and stereoselectivity are also addressed.
- Wong, Henry N. C.
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p. 1757 - 1765
(2007/10/03)
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