Biomimetic Total Syntheses of (-)-TAN1251A, (+)-TAN1251B, (+)-TAN1251C, and (+)-TAN1251D

被引：35

作者：

Snider, BB ^{[1
]}

Lin, H ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem MS 015, Waltham, MA 02254 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 05期

关键词：

D O I：

10.1021/ol991401q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The muscarinic antagonists (-)-TAN1251A (1), (+)-TAN1251B (2), (+)-TAN1251C (3), and (+)-TAN1251D (4) have been synthesized biomimetically by enamine formation from an amino aldehyde to give TAN1251C ketal 18, Oxidation and reduction lead to TAN1251A (1), which has been hydroxylated to give TAN1251B (2), Stereospecific reduction of TAN1251C ketal 18 leads to TAN1251D (4).

引用

页码：643 / 646

页数：4

共 17 条

[11] ACID-CATALYZED HYDROLYSIS OF CYCLIC BENZOPHENONE ACETALS - EFFECTS OF RING SIZE AND RING SUBSTITUENT [J].

OSHIMA, T ;

UENO, SY ;

NAGAI, T .

HETEROCYCLES, 1995, 40 (02) :607-617

[12] FR901483, a novel immunosuppressant isolated from Cladobotryum sp No 11231 - Taxonomy of the producing organism, fermentation, isolation, physico-chemical properties and biological activities [J].

Sakamoto, K ;

Tsujii, E ;

Abe, F ;

Nakanishi, T ;

Yamashita, M ;

Shigematsu, N ;

Izumi, S ;

Okuhara, M .

JOURNAL OF ANTIBIOTICS, 1996, 49 (01) :37-44

[13]

SHIRAFUJI H, 1991, Patent No. 13887

[14] GEM-DIALKYL EFFECT .2. A COMPARISON OF KINETIC AND EQUILIBRIUM APPROACHES TO SELECTIVE KETALIZATION OF 5ALPHA-ANDROSTANE-3,17-DIONE WITH VARIOUS GLYCOLS [J].

SMITH, SW ;

NEWMAN, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (05) :1249-&

[15] GEM-DIALKYL EFFECT .3. KINETIC AND EQUILIBRIUM STUDIES OF STEROID CYCLIC KETAL FORMATION AND HYDROLYSIS [J].

SMITH, SW ;

NEWMAN, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (05) :1253-&

[16] Total synthesis of (-)-FR901483 [J].

Snider, BB ;

Lin, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (34) :7778-7786

[17] Synthesis of desmethylamino FR901483 [J].

Snider, BB ;

Lin, H ;

Foxman, BM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6442-6443

← 1 2 →