Photooxidations of 2-(γ,ε-Dihydroxyalkyl) Furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins

被引：22

作者：

Kouridaki, Antonia ^{[1
]}

Montagnon, Tamsyn ^{[1
]}

Tofi, Maria ^{[1
]}

Vassilikogiannakis, Georgios ^{[1
]}

机构：

[1] Univ Crete, Dept Chem, Iraklion 71003, Crete, Greece

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 09期

基金：

欧洲研究理事会;

关键词：

SINGLET OXYGEN; ASYMMETRIC SYNTHESES; RING-SYSTEM; SECO ACID; PART II; ONE-POT; FRAGMENT; IDENTIFICATION; APOPTOSIS; PRODUCTS;

D O I：

10.1021/ol3007937

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photooxygenations of 2-(gamma,epsilon-dihydroxyalkyl) furans in H2O followed by in situ reduction and ketalization affords, in one synthetic operation, DE-bicyclic ketals of the pectenotoxins.

引用

页码：2374 / 2377

页数：4

共 41 条

[21] Synthesis of the FG ring fragment of pectenotoxins 1-9 [J].

Heapy, Amanda M. ;

Brimble, Margaret A. .

TETRAHEDRON, 2010, 66 (29) :5424-5431

[22] Synthetic studies toward pectenotoxin 2. Part II. Synthesis of the CDE and CDEF ring systems [J].

Helmboldt, Hannes ;

Aho, Jatta E. ;

Pihko, Petri M. .

ORGANIC LETTERS, 2008, 10 (19) :4183-4185

[23] Spirodiepoxide Strategy to the C Ring of Pectenotoxin 4: Synthesis of the C1-C19 Sector [J].

Joyasawal, Sipak ;

Lotesta, Stephen D. ;

Akhmedov, N. G. ;

Williams, Lawrence J. .

ORGANIC LETTERS, 2010, 12 (05) :988-991

[24] Mukaiyama-Michael Reactions with Acrolein and Methacrolein: A Catalytic Enantioselective Synthesis of the C17-C28 Fragment of Pectenotoxins [J].

Kemppainen, Eeva K. ;

Sahoo, Gokarneswar ;

Valkonen, Arto ;

Pihko, Petri M. .

ORGANIC LETTERS, 2012, 14 (04) :1086-1089

[25] Synthesis of the C21-C28 segment of pectenotoxin-4 [J].

Kolakowski, Robert V. ;

Williams, Lawrence J. .

TETRAHEDRON LETTERS, 2007, 48 (27) :4761-4764

[26] A spirodiepoxide-based strategy to the A-B ring system of pectenotoxin 4 [J].

Lotesta, Stephen D. ;

Hou, Yongquan ;

Williams, Lawrence J. .

ORGANIC LETTERS, 2007, 9 (05) :869-872

[27] Studies on the synthesis of pectenotoxin II: Synthesis of a C(11)-C(26) fragment precursor via [3+2]-annulation reactions of chiral allylsilanes [J].

Micalizio, GC ;

Roush, WR .

ORGANIC LETTERS, 2001, 3 (12) :1949-1952

[28] Isolation and identification of pectenotoxins-13 and -14 from Dinophysis acuta in New Zealand [J].

Miles, Christopher Owen ;

Wilkins, Alistair L. ;

Hawkes, Allan D. ;

Jensen, Dwayne J. ;

Selwood, Andrew I. ;

Beuzenberg, Veronica ;

MacKenzie, A. Lincoln ;

Cooney, Janine M. ;

Holland, Patrick T. .

TOXICON, 2006, 48 (02) :152-159

[29] Using singlet oxygen to synthesize polyoxygenated natural products from Furans [J].

Montagnon, Tamsyn ;

Tofi, Maria ;

Vassilikogiannakis, Georgios .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (08) :1001-1011

[30] Green oxidations of furans-initiated by molecular oxygen-that give key natural product motifs [J].

Montagnon, Tamsyn ;

Noutsias, Dimitris ;

Alexopoulou, Ioanna ;

Tofi, Maria ;

Vassilikogiannakis, Georgios .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (07) :2031-2039

← 1 2 3 4 5 →