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  Total Synthesis of Woodrosin I—Part 1: Preparation of the Building Blocks and Evaluation of the Glycosylation Strategy

Fürstner, A., Jeanjean, F., Razon, P., Wirtz, C., & Mynott, R. (2003). Total Synthesis of Woodrosin I—Part 1: Preparation of the Building Blocks and Evaluation of the Glycosylation Strategy. Chemistry – A European Journal, 9(1), 307-319. doi:10.1002/chem.200390025.

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 Creators:
Fürstner, Alois1, Author              
Jeanjean, Fabien1, Author              
Razon, Patrick1, Author              
Wirtz, Cornelia2, Author              
Mynott, Richard2, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Service Department Mynott (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445627              

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Free keywords: carbohydrates, glycolipids, glycosides, macrolides, natural product's
 Abstract: The completion of the first total synthesis of the complex resin glycoside woodrosin I (1) is outlined using the building blocks described in the preceding paper. Key steps involve the TMSOTf-catalyzed coupling of diol 2 with trichloroacetimidate 3 which leads to the selective formation of orthoester 5 rather than to the expected tetrasaccharide. Diene 5, on treatment with catalytic amounts of the Grubbs carbene complex 6 or the phenylindenylidene ruthenium complex 7, undergoes a high yielding ring closing olefin metathesis reaction (RCM) to afford macrolide 8. Exposure of the latter to the rhamnosyl donor 4 in the presence of TMSOTf under “inverse glycosylation” conditions delivers compound 9 by a process involving glycosylation of the sterically hindered 2′-OH group and concomitant rearrangement of the adjacent orthoester into the desired β-glycoside. This transformation constitutes one of the most advanced applications of the Kochetkov glycosidation method reported to date. Cleavage of the chloroacetate followed by exhaustive hydrogenation completes the total synthesis of the targeted glycolipid 1.

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Language(s): eng - English
 Dates: 2002-08-062002-12-302003-01-03
 Publication Status: Published in print
 Pages: 13
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: eDoc: 119463
DOI: 10.1002/chem.200390025
ISI: 000180368600027
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: - Volume / Issue: 9 (1) Sequence Number: - Start / End Page: 307 - 319 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058