Chemo-enzymatic synthesis of the C15–C23 unit of Leptomycin B

Michael Scheck; Herbert Waldmann

doi:10.1139/v02-070

Chemo-enzymatic synthesis of the C15C23 unit of Leptomycin B

Canadian Journal of Chemistry ◽

10.1139/v02-070 ◽

2002 ◽

Vol 80 (6) ◽

pp. 571-576 ◽

Cited By ~ 3

Author(s):

Michael Scheck ◽

Herbert Waldmann

Keyword(s):

Asymmetric Synthesis ◽

Natural Product ◽

Building Block ◽

Enzymatic Synthesis ◽

Aldol Reaction ◽

Natural Product Synthesis ◽

Leptomycin B ◽

Enzymatic Transformation

The asymmetric synthesis of the C15C23 unit of Leptomycin B (LMB) is described. All four stereocenters of the C15C23 unit were prepared from one building block exhibiting only one stereocenter. This building block was synthesized via either an enzymatic transformation or starting from a chiral reagent.Key words: Leptomycin, natural product synthesis, enzymatic transformation, Aldol reaction, Pseudomonas fluorescence lipase (PFL).

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Chiral synthesis of polyketide-derived natural products. 44. Large Laboratory scale Synthesis of (2S,3S)-2-(4-Methoxybenzyloxy)-3,4-O-(3-pentylidene)-1,3,4-butantriol, a Versatile Chiral Building Block in Natural Product Synthesis.

Chemical and Pharmaceutical Bulletin ◽

10.1248/cpb.42.683 ◽

1994 ◽

Vol 42 (3) ◽

pp. 683-685 ◽

Cited By ~ 4

Author(s):

Kiyoshi HORITA ◽

Youji SAKURAI ◽

Shun-ichiro HACHIYA ◽

Masaaki NAGASAWA ◽

Osamu YONEMITSU

Keyword(s):

Natural Products ◽

Natural Product ◽

Building Block ◽

Laboratory Scale ◽

Natural Product Synthesis ◽

Chiral Synthesis ◽

Chiral Building Block

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Synthetic Approaches to Enantiomerically Enriched 4-Hydroxycyclohex-2-en-1-one - A Key Chiral Building Block in Complex Natural Product Synthesis

Synthesis ◽

10.1055/s-0030-1258335 ◽

2010 ◽

Vol 2011 (05) ◽

pp. 681-707 ◽

Cited By ~ 1

Author(s):

Richard Taylor ◽

Alan Burns

Keyword(s):

Natural Product ◽

Building Block ◽

Natural Product Synthesis ◽

Chiral Building Block ◽

Synthetic Approaches

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The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis

Natural Product Reports ◽

10.1039/c3np70102f ◽

2014 ◽

Vol 31 (4) ◽

pp. 563-594 ◽

Cited By ~ 81

Author(s):

Markus Kalesse ◽

Martin Cordes ◽

Gerrit Symkenberg ◽

Hai-Hua Lu

Keyword(s):

Natural Product ◽

Aldol Reaction ◽

Natural Product Synthesis ◽

Mukaiyama Aldol Reaction ◽

Mukaiyama Aldol ◽

Recent Developments

This review will provide an overview on the recent developments of polyketide synthesis using the vinylogous Mukaiyama aldol reaction for the construction of advanced intermediates. In general, four different motifs can be constructed efficiently using the recent developments of asymmetric variants of this strategy.

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ChemInform Abstract: Enzymatic Preparation of Optically Active 2-Acetoxymethylglycidol. A New Chiral Building Block in Natural Product Synthesis.

ChemInform ◽

10.1002/chin.199315166 ◽

2010 ◽

Vol 24 (15) ◽

pp. no-no

Author(s):

Y.-B. SEU ◽

Y.-H. KHO

Keyword(s):

Natural Product ◽

Building Block ◽

Optically Active ◽

Natural Product Synthesis ◽

Enzymatic Preparation ◽

Chiral Building Block

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The Aldol Reaction in Natural Product Synthesis. The Epothilone Story

ChemInform ◽

10.1002/chin.200538245 ◽

2005 ◽

Vol 36 (38) ◽

Author(s):

Dieter Schinzer

Keyword(s):

Natural Product ◽

Aldol Reaction ◽

Natural Product Synthesis

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Asymmetric Synthesis Using Chiral Acetals from C2-Symmetric Diols and Its Application to Natural Product Synthesis

Stereoselective Synthesis (Part I) - Studies in Natural Products Chemistry - Studies in Natural Products Chemistry ◽

10.1016/b978-0-444-81780-8.50018-1 ◽

1994 ◽

pp. 469-516 ◽

Cited By ~ 4

Author(s):

Hiromichi Fujioka ◽

Yasuyuki Kita

Keyword(s):

Asymmetric Synthesis ◽

Natural Product ◽

Natural Product Synthesis

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Catalytic Asymmetric Synthesis of Both syn- and anti-3,5-Dihydroxy Esters: Application to 1,3-Polyol/α-Pyrone Natural Product Synthesis.

ChemInform ◽

10.1002/chin.200325032 ◽

2003 ◽

Vol 34 (25) ◽

Author(s):

Shin-ya Tosaki ◽

Tetsuhiro Nemoto ◽

Takashi Ohshima ◽

Masakatsu Shibasaki

Keyword(s):

Asymmetric Synthesis ◽

Natural Product ◽

Natural Product Synthesis ◽

Catalytic Asymmetric Synthesis ◽

Catalytic Asymmetric

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ChemInform Abstract: Hagemann′s Ester: A Timeless Building Block for Natural Product Synthesis

ChemInform ◽

10.1002/chin.201029235 ◽

2010 ◽

Vol 41 (29) ◽

pp. no-no

Author(s):

Gian Piero Pollini ◽

Simonetta Benetti ◽

Carmela De Risi ◽

Vinicio Zanirato

Keyword(s):

Natural Product ◽

Building Block ◽

Natural Product Synthesis

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Catalytic Asymmetric Synthesis of Bothsyn- andanti-3,5-Dihydroxy Esters: Application to 1,3-Polyol/α-Pyrone Natural Product Synthesis

Organic Letters ◽

10.1021/ol0273708 ◽

2003 ◽

Vol 5 (4) ◽

pp. 495-498 ◽

Cited By ~ 42

Author(s):

Shin-ya Tosaki ◽

Tetsuhiro Nemoto ◽

Takashi Ohshima ◽

Masakatsu Shibasaki

Keyword(s):

Asymmetric Synthesis ◽

Natural Product ◽

Natural Product Synthesis ◽

Catalytic Asymmetric Synthesis ◽

Catalytic Asymmetric

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Hagemann's ester: a timeless building block for natural product synthesis

Tetrahedron ◽

10.1016/j.tet.2010.01.078 ◽

2010 ◽

Vol 66 (15) ◽

pp. 2775-2802 ◽

Cited By ~ 16

Author(s):

Gian Piero Pollini ◽

Simonetta Benetti ◽

Carmela De Risi ◽

Vinicio Zanirato

Keyword(s):

Natural Product ◽

Building Block ◽

Natural Product Synthesis

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Chemo-enzymatic synthesis of the C15C23 unit of Leptomycin B

Chiral synthesis of polyketide-derived natural products. 44. Large Laboratory scale Synthesis of (2S,3S)-2-(4-Methoxybenzyloxy)-3,4-O-(3-pentylidene)-1,3,4-butantriol, a Versatile Chiral Building Block in Natural Product Synthesis.

Synthetic Approaches to Enantiomerically Enriched 4-Hydroxycyclohex-2-en-1-one - A Key Chiral Building Block in Complex Natural Product Synthesis

The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis

ChemInform Abstract: Enzymatic Preparation of Optically Active 2-Acetoxymethylglycidol. A New Chiral Building Block in Natural Product Synthesis.

The Aldol Reaction in Natural Product Synthesis. The Epothilone Story

Asymmetric Synthesis Using Chiral Acetals from C2-Symmetric Diols and Its Application to Natural Product Synthesis

Catalytic Asymmetric Synthesis of Both syn- and anti-3,5-Dihydroxy Esters: Application to 1,3-Polyol/α-Pyrone Natural Product Synthesis.

ChemInform Abstract: Hagemann′s Ester: A Timeless Building Block for Natural Product Synthesis

Catalytic Asymmetric Synthesis of Bothsyn- andanti-3,5-Dihydroxy Esters: Application to 1,3-Polyol/α-Pyrone Natural Product Synthesis

Hagemann's ester: a timeless building block for natural product synthesis

Chemo-enzymatic synthesis of the C15C23 unit of Leptomycin B