Literature DB >> 20513158

Total synthesis of (+/-)-aplykurodinone-1: traceless stereochemical guidance.

Yandong Zhang1, Samuel J Danishefsky.   

Abstract

The total synthesis of the highly degraded steroidal natural product, aplykurodinone-1 (1), has been accomplished. Key features include a one-flask hydrolysis/retro-aldol/iodolactonization sequence to excise the C(8) hydroxymethylene functionality with retention of stereochemistry and the stereoselective installation of the C(13) methyl group through hydrogenation with homogeneous catalyst.

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Year:  2010        PMID： 20513158      PMCID： PMC2912429          DOI： 10.1021/ja1035495

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  13 in total

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7.  3-Epi-aplykurodinone B, a new degraded sterol from Aplysia fasciata.

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8.  Vitamin D3 metabolites. II. Further syntheses of 25-hydroxycholesterol.

Authors:  T A Narwid; K E Cooney; M R Uskoković
Journal:  Helv Chim Acta       Date:  1974-04-27       Impact factor: 2.164

9.  Using correlations to compare additions to alkenes: homogeneous hydrogenation by using Wilkinson's catalyst.

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10.  4-acetylaplykurodin B and aplykurodinone B, two ichthyotoxic degraded sterols from the Mediterranean mollusk Aplysia fasciata.

Authors:  A Spinella; M Gavagnin; A Crispino; G Cimino; E Martinez; J Ortea; G Sodano
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  12 in total

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6.  Effect of protic additives in Cu-catalysed asymmetric Diels-Alder cycloadditions of doubly activated dienophiles: towards the synthesis of magellanine-type Lycopodium alkaloids.

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8.  Iridium-Catalyzed Enantioselective Allylic Substitution of Enol Silanes from Vinylogous Esters and Amides.

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Review 9.  Cross-coupling reactions towards the synthesis of natural products.

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10.  Strain-Release Heteroatom Functionalization: Development, Scope, and Stereospecificity.

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Journal:  J Am Chem Soc       Date:  2017-02-20       Impact factor: 15.419
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