An approach to the anhydride unit of CP-225,917 and CP-263,114

被引：20

作者：

Clive, DLJ ^{[1
]}

Sun, SY ^{[1
]}

Gagliardini, V ^{[1
]}

Sano, MK ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 33期

基金：

加拿大自然科学与工程研究理事会;

关键词：

anhydride; siloxy-Cope rearrangement; Tebbe reagent; bridgehead olefin; quaternary carbon;

D O I：

10.1016/S0040-4039(00)01065-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Compound 1, representing the core structure of CP-225,917, including the anhydride subunit, was prepared by an approach involving siloxy-Cope rearrangement of the strained lactone 18, in which C(15) of the anhydride is already present. The C(14) carbon was introduced at a later stage with the Tebbe reagent. Further elaboration gave homoallylic alcohol 25, which was converted into epoxy aldehyde 27, and then into furan 28. This was transformed efficiently into 1 by the successive action of singlet oxygen, DBU and TPAP. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：6259 / 6263

页数：5

共 29 条

[11] A concise total synthesis of dysidiolide through application of a dioxolenium-mediated Diels-Alder reaction [J].

Magnuson, SR ;

Sepp-Lorenzino, L ;

Rosen, N ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (07) :1615-1616

[12] PARA-ANISYLOXYMETHYL GROUP, A NOVEL OXIDATIVELY REMOVABLE ACETAL TYPE OH-PROTECTING GROUP [J].

MASAKI, Y ;

IWATA, I ;

MUKAI, I ;

ODA, H ;

NAGASHIMA, H .

CHEMISTRY LETTERS, 1989, (04) :659-662

[13]

Meng DF, 1999, ANGEW CHEM INT EDIT, V38, P3197, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3197::AID-ANIE3197>3.0.CO

[14]

2-6

[15]

Nicolaou KC, 2000, ANGEW CHEM INT EDIT, V39, P1829, DOI 10.1002/(SICI)1521-3773(20000515)39:10<1829::AID-ANIE1829>3.0.CO

[16]

2-6

[17] Novel strategies to construct the γ-hydroxy lactone moiety of the CP molecules.: Synthesis of the CP-225,917 core skeleton [J].

Nicolaou, KC ;

He, Y ;

Fong, KC ;

Yoon, WH ;

Choi, HS ;

Zhong, YL ;

Baran, PS .

ORGANIC LETTERS, 1999, 1 (01) :63-66

[18]

Nicolaou KC, 1999, ANGEW CHEM INT EDIT, V38, P1676, DOI 10.1002/(SICI)1521-3773(19990601)38:11<1676::AID-ANIE1676>3.0.CO

[19]

2-T

[20]

Nicolaou KC, 1999, ANGEW CHEM INT EDIT, V38, P549, DOI 10.1002/(SICI)1521-3773(19990215)38:4<549::AID-ANIE549>3.0.CO

← 1 2 3 →