Enantioselective Synthesis of a Diastereomer of Iriomoteolide-1a. What Is the Correct Structure of the Natural Product?

被引：24

作者：

Fang, Lijing ^{[1
]}

Yang, Jiong ^{[1
]}

Yang, Fei ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 14期

关键词：

OLEFIN-METATHESIS CATALYSTS; STRUCTURE ELUCIDATION; BIOACTIVE MACROLIDES; C-13-C23; FRAGMENT; NMR; REAGENTS; CONFIGURATION; AMPHIDINIUM; AMPHIDINOLIDES; CONSTRUCTION;

D O I：

10.1021/ol1011423

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective approach to a diastereomer of iriomoteolide-1a is described. Highlighted is a Sml(2)-mediated intramolecular reductive cyclization approach to complex cyclic hemiketals. An acetylide-chloroformate coupling strategy is also featured. Our results show that the structures of iriomoteolide-1a-1c require careful reassessment.

引用

页码：3124 / 3127

页数：4

共 54 条

[1] Stereoselective syntheses of the C(1)-C(9) fragment of amphidinolide C
Bates, Robert H.
Shotwell, J. Brad
Roush, William R.
[J]. ORGANIC LETTERS, 2008, 10 (19) : 4343 - 4346
[2] Determination of relative configuration in organic compounds by NMR spectroscopy and computational methods
Bifulco, Giuseppe
Dambruoso, Paolo
Gomez-Paloma, Luigi
Riccio, Raffaele
[J]. CHEMICAL REVIEWS, 2007, 107 (09) : 3744 - 3779
[3] ENANTIOMERIC (Z)-CROTYLDIISOPINOCAMPHEYLBORANE AND (E)-CROTYLDIISOPINOCAMPHEYLBORANE - SYNTHESIS IN HIGH OPTICAL PURITY OF ALL 4 POSSIBLE STEREOISOMERS OF BETA-METHYLHOMOALLYL ALCOHOLS
BROWN, HC
BHAT, KS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (02) : 293 - 294
[4] CHIRAL SYNTHESIS VIA ORGANOBORANES .7. DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF ERYTHRO-BETA-METHYLOMOALLYL AND THREO-BETA-METHYLHOMOALLYL ALCHOLS VIA ENANTIOMERIC (Z)-CROTYLBORANE AND (E)-CROTYLBORANE
BROWN, HC
BHAT, KS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) : 5919 - 5923
[5] Synthesis of Iriomoteolide-1a C13-C23 Fragment via Asymmetric Conjugate Addition and Julia-Kocienski Coupling Reaction
Chin, Yen-Jin
Wang, Shun-Yi
Loh, Teck-Peng
[J]. ORGANIC LETTERS, 2009, 11 (16) : 3674 - 3676
[6] Coleman RS, 2001, ANGEW CHEM INT EDIT, V40, P1736, DOI 10.1002/1521-3773(20010504)40:9<1736::AID-ANIE17360>3.0.CO
[7] 2-#
[8] A NEW STEREOSPECIFIC SYNTHESIS OF TRISUBSTITUTED AND TETRASUBSTITUTED OLEFINS . CONJUGATE ADDITION OF DIALKYLCOPPER-LITHIUM REAGENTS TO ALPHA,BETA-ACETYLENIC ESTERS
COREY, EJ
KATZENEL.JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (07) : 1851 - &
[9] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis
Deiters, A
Martin, SF
[J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2199 - 2238
[10] Fang L., UNPUB

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