Bioinspired Total Synthesis and Stereochemical Revision of the Fungal Metabolite Pestalospirane B

被引：10

作者：

Badrinarayanan, Sandhya ^{[1
]}

Squire, Christopher J. ^{[2
]}

Sperry, Jonathan ^{[1
]}

Brimble, Margaret A. ^{[1
,2
,3
]}

机构：

[1] Univ Auckland, Sch Chem Sci, 23 Symonds St, Auckland, New Zealand

[2] Univ Auckland, Sch Biol Sci, 3A Symonds St, Auckland, New Zealand

[3] Maurice Wilkins Ctr Mol Biodiscovery, 3 Symonds St, Auckland, New Zealand

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 13期

关键词：

HPLC-SPE-NMR; DERIVATIVES; REDUCTION; EFFICIENT;

D O I：

10.1021/acs.orglett.7b01371

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of both enantiomers of pestalospirane B, 2, has been achieved using a bioinspired tandem dimerization-spiroketalization reaction. Electronic circular dichroism (ECD) and X-ray analysis were used to revise the absolute stereochemistry of the natural product pestalospirane B from 3S, 3'S, 12R, 12'R to its enantiomer 3R, 3'R, 12S, 12'S.

引用

页码：3414 / 3417

页数：4

共 23 条

[1]

[Anonymous], 2010, COMPREHENSIVE ORGANI

[2] Efficient and selective reduction protocols of the 2,2-dimethyl-1,3-benzodioxan-4-one functional group to readily provide both substituted salicylaldehydes and 2-hydroxybenzyl alcohols [J].

Bajwa, N ;

Jennings, MP .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09) :3646-3649

[3]

Banerjee AK, 2006, J SCI IND RES INDIA, V65, P299

[4]

BOUILLANT ML, 1989, Z NATURFORSCH C, V44, P719

[5]

BURN D, 1960, TETRAHEDRON LETT, P14

[6] Controlled semihydrogenation of aminoalkynes using ethylenediamine as a poison of Lindlar's catalyst [J].

Campos, KR ;

Cai, DW ;

Journet, M ;

Kowal, JJ ;

Larsen, RD ;

Reider, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (10) :3634-3635

[7] Recent advances in Sonogashira reactions [J].

Chinchilla, Rafael ;

Najera, Carmen .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5084-5121

[8] Recent advances in the synthetic applications of the oxazaborolidine-mediated asymmetric reduction [J].

Cho, Byung Tae .

TETRAHEDRON, 2006, 62 (33) :7621-7643

[9] AN EFFICIENT AND CATALYTICALLY ENANTIOSELECTIVE ROUTE TO (S)-(-)-PHENYLOXIRANE [J].

COREY, EJ ;

SHIBATA, S ;

BAKSHI, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2861-2863

[10]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO

← 1 2 3 →