Synthesis of (S)-manoalide diol and the absolute configuration of natural manoalide

Amoo, Victor E.; Bernardo, Silvano De; Weigele, Manfred

doi:10.1016/s0040-4039(00)87892-2

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Sesterterpenes1

Absolute Configuration Of Manoalide and Related Naturally Oc1

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2018

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Cited by 30 publications

(16 citation statements)

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“…30 Rapid tautomerisation prevents the determination of the stereochemistry at the two hemi-acetal centers of 24 while the R configuration at the third asymmetric center was established after comparison of the CD spectrum of the reduction product of 24 with that of a synthetic analogue. 31 A comprehensive review of the isolation, biosynthesis, synthesis and biological activity of 24 and its analogues has been published. 32 There has been much interest in the biological activity of manoalide (24).…”

Section: Sesterterpenesmentioning

confidence: 99%

Anti-inflammatory metabolites from marine sponges

2005

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Section: Sesterterpenesmentioning

confidence: 99%

Anti-inflammatory metabolites from marine sponges

2005

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“…The absolute configuration at C-4 in manoalide (1) was established by Amoo et al [17] to be R by reduction to manoalide diol (16) and comparison of the CD spectrum of the latter with that of the synthetic (S)-enantiomer prepared from 2-deoxy--ribose. The same result was later obtained by the Horeau method and the modified Mosher method.…”

Section: Absolute Configuration Of Manoalide and Related Naturally Ocmentioning

confidence: 99%

Stereochemistry of Antiinflammatory Marine Sesterterpenes

et al. 2000

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The absolute configuration of antiinflammatory marine sesterterpenes belonging to the manoalide and cacospongionolide structural type has been determined by comparison of the CD spectra of the natural compounds with those of analogues that have been stereoselectively synthesized. In the derived acetates the relative stereochemistry of the stereogenic centres in the pyranofuranone moiety is assigned from 1H‐NMR data and the absolute configuration from CD spectra. The absolute configuration of the naturally occurring marine sesterterpenes thorectolide monoacetate, manoalide monoacetate, petrosaspongiolide M and cavernosolide has been determined.

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“…The overall yield of our synthesis compares favourably with previous syntheses. [10][11][12][13][14] We thank the EPSRC for financial support, Dr Michael Garst for NMR spectra of authentic manoalide and Rhonan Ford for technical advice.…”

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confidence: 99%