Stereoselective Synthesis of 2-Isocyanoallopupukeanane

Ho, Tse‐Lok; Kung, Liang-Rern

doi:10.1021/ol990181d

Cited by 10 publications

(3 citation statements)

References 8 publications

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“…401,402 Only one racemic synthesis of (±)-2-isocyanoallopupukeanane 239 has been reported to date (Scheme 33). 403,404 Lactone 498, prefiguring the final cyclopentane−cyclohexane-bridged skeleton, was obtained in 56% yield via a ring-expansion process, starting from ester 497.…”

Section: Synthesismentioning

confidence: 99%

Tricyclic Sesquiterpenes from Marine Origin

et al. 2017

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The structure elucidation, biosynthesis, and biological activity of marine carbotricyclic sesquiterpene compounds are reviewed from the pioneering results to the end of 2015. Their total syntheses with a particular emphasis on the first syntheses, enantiomeric versions, and syntheses that led to the revision of structures or stereochemistries are summarized. Overall, 284 tricyclic compounds are classified into fused, bridged, and miscellaneous structures based on 54 different skeletal types. Tricyclic sesquiterpenes constitute an important group of natural products. Their structural diversity and biological activities have generated further interest in the field of drug discovery research, although the exact mechanisms of action of these species are not well known. Furthermore, these tricyclic structures, according to their chemical complexity, are a source of inspiration for chemists in the field of total synthesis for the development of innovative methodologies.

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Section: Synthesismentioning

confidence: 99%

Tricyclic Sesquiterpenes from Marine Origin

et al. 2017

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“…527 2-Isocyanoallopupukeanane 766, which is a metabolite of the nudibranch Phyllidia pustulosa from Japan, 528 has been synthesized in good yield using an intramolecular Diels-Alder reaction to fuse the bridging cyclopentane ring to a bicyclo[3.2.1]octane unit. 529 The Okinawan nudibranch Reticulidia fungia contained two additional members of a rare class of sponge metabolites, the carbonimidic dichlorides reticulidins A 767 and B 768. 530 The absolute stereochemistry of the farnesic acid glyceride derivatives 769-771 from Archidoris odhneri 531 and the drimane derivatives 772 and 773 from A. montereyensis 532 were determined by total synthesis.…”

Section: Molluscsmentioning

confidence: 99%

Marine natural products (1999)

2001

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“…Our involvement in this area of chemistry has resulted in the synthesis of curcuphenol and curcudiol, (−)-furodysin, (−)-furodysinin, the enantiomer of herbasolide, and tavacpallescensin . More recently, efforts in attaining the isocyanopupukeananes also bore fruit; we now describe our approach to 9-isocyanoneopupukeanane ( 1 ), which is a constituent of a Ciocalypta sp . Besides the syntheses of 2-isocyanopupukeanane ( 2a , Chart ) and 9-isocyanopupukeanane ( 2b ), , formal syntheses of the latter that terminated at 9-pupukeanone − have also been reported.…”

mentioning

confidence: 99%