A Convergent Approach toward the C1-C11 Subunit of Phoslactomycins and Formal Synthesis of Phoslactomycin B

被引：41

作者：

Druais, Valerie ^{[1
]}

Hall, Michael J. ^{[1
]}

Corsi, Camilla ^{[2
]}

Wendeborn, Sebastian V. ^{[2
]}

Meyer, Christophe ^{[1
]}

Cossy, Janine ^{[1
]}

机构：

[1] ESPCI ParisTech, Chim Organ Lab, CNRS, F-75231 Paris 05, France

[2] Syngenta Crop Protect Muenchwilen AG, CH-4332 Stein, Switzerland

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 04期

关键词：

RING-CLOSING METATHESIS; PROTEIN PHOSPHATASE 2A; ANTITUMOR ANTIBIOTIC PHOSPHOLINE; COLONY-STIMULATING FACTORS; FAMILY INDUCE PRODUCTION; MARROW STROMAL CELLS; LEUSTRODUCSIN-B; SIGMATROPIC REARRANGEMENTS; MICROBIAL METABOLITES; ASYMMETRIC CATALYSIS;

D O I：

10.1021/ol8029142

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of the C1-C11 subunit of phoslactomycins, and a formal synthesis of phoslactomycin B, were achieved by a convergent strategy involving the chelation-controlled addition of an alkynyl Grignard reagent to an alpha-alkoxy ketone. Catalytic enantioselective reductions of acetylenic ketones and a [2,3]-Wittig rearrangement were utilized as key steps to control the configuration of the C4, C5, and C9 stereocenters.

引用

页码：935 / 938

页数：4

共 43 条

[1] REGIO-SPECIFIC AND STEREO-SPECIFIC REDUCTION OF CONJUGATED AND NON-CONJUGATED TRIPLE BONDS BY ACTIVATED ZINC POWDER [J].

AERSSENS, MHPJ ;

BRANDSMA, L .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (12) :735-736

[2] AN EFFICIENT SYNTHESIS OF NOVEL ALPHA-DIKETONE AND ALPHA-KETO ESTER DERIVATIVES OF N-PROTECTED AMINO-ACIDS AND PEPTIDES [J].

ANGELASTRO, MR ;

PEET, NP ;

BEY, P .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16) :3913-3916

[3]

Bialy L, 2002, SYNTHESIS-STUTTGART, P2096

[4] Short synthesis of the C1-C14 stretch of discodermolide from building blocks prepared by asymmetric catalysis [J].

Cao, Huanyan ;

Parker, Kathlyn A. .

ORGANIC LETTERS, 2008, 10 (07) :1353-1356

[5] SYNTHETIC STUDIES ON (2R,4'R,8'R)-ALPHA-TOCOPHEROL FACILE SYNTHESES OF OPTICALLY-ACTIVE, SATURATED, ACYCLIC ISOPRENOIDS VIA STEREOSPECIFIC [3,3] SIGMATROPIC REARRANGEMENTS [J].

CHAN, KK ;

COHEN, N ;

DENOBLE, JP ;

SPECIAN, AC ;

SAUCY, G .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (22) :3497-3505

[6]

Chavez DE, 2001, ANGEW CHEM INT EDIT, V40, P3667, DOI 10.1002/1521-3773(20011001)40:19<3667::AID-ANIE3667>3.0.CO

[7]

2-6

[8] (E)-3-(TRIMETHYLSILYL)-2-PROPEN-1-OL - AN IMPROVED PREPARATION [J].

DENMARK, SE ;

JONES, TK .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (23) :4595-4597

[9] STUDIES ON NEW PHOSPHATE ESTER ANTIFUNGAL ANTIBIOTICS PHOSLACTOMYCINS .2. STRUCTURE ELUCIDATION OF PHOSLACTOMYCIN-A TO PHOSLACTOMYCIN-F [J].

FUSHIMI, S ;

FURIHATA, K ;

SETO, H .

JOURNAL OF ANTIBIOTICS, 1989, 42 (07) :1026-1036

[10] Relay ring-closing metathesis (RRCM): A strategy for directing metal movement throughout olefin metathesis sequences [J].

Hoye, TR ;

Jeffrey, CS ;

Tennakoon, MA ;

Wang, JZ ;

Zhao, HY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (33) :10210-10211

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