Stereocontrolled Total Synthesis of Sphingofungin E

被引：23

作者：

Ikeuchi, Kazutada ^{[1
]}

Hayashi, Moemi ^{[1
]}

Yamamoto, Tomohiro ^{[1
]}

Inai, Makoto ^{[1
]}

Asakawa, Tomohiro ^{[1
]}

Hamashima, Yoshitaka ^{[1
]}

Kan, Toshiyuki ^{[1
]}

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 30期

关键词：

Asymmetric synthesis; Olefination; Oxidation; Rearrangement; Amino acids; BENZYL PROTECTIVE GROUP; OXIDATION; IMMUNOSUPPRESSANT; HYDROGENOLYSIS; REARRANGEMENT; MYRIOCIN;

D O I：

10.1002/ejoc.201301065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe herein the asymmetric total synthesis of sphingofungin E, which has potent immunosuppressive activity. Key steps include asymmetric desymmetrization by bromolactonization, stereocontrolled construction of four contiguous stereogenic centers through allylic C-H oxidation and epoxide ring opening, regioselective elongation of a dialdehyde, and Hofmann rearrangement by using PhI(OCOCF3)(2).

引用

页码：6789 / 6792

页数：4

共 50 条

[1] Total synthesis of sphingofungin E
Nakamura, T
Shiozaki, M
TETRAHEDRON LETTERS, 2001, 42 (14) : 2701 - 2704
[2] Total Synthesis of Sphingofungin E and 4,5-Di-epi-sphingofungin E
Noda, Narumi
Nambu, Hisanori
Fujiwara, Tomoya
Yakura, Takayuki
CHEMICAL & PHARMACEUTICAL BULLETIN, 2017, 65 (07) : 687 - 696
[3] Total synthesis of sphingofungin E from D-glucose
Oishi, T
Ando, K
Inomiya, K
Sato, H
Iida, M
Chida, N
ORGANIC LETTERS, 2002, 4 (01) : 151 - 154
[4] The first total synthesis of sphingofungin E and the determination of its stereochemistry
Wang, B
Yu, XM
Lin, GQ
SYNLETT, 2001, : 904 - 906
[5] Total synthesis of sphingofungin F
Li, Min
Wu, Anmei
SYNLETT, 2006, (18) : 2985 - 2988
[6] Total synthesis of sphingofungin F
Lee, KY
Oh, CY
Ham, WH
ORGANIC LETTERS, 2002, 4 (25) : 4403 - 4405
[7] Total synthesis of sphingofungin E from D-glucose derivative
Nakamura, T
Shiozaki, M
TETRAHEDRON, 2002, 58 (43) : 8779 - 8791
[8] Highly stereocontrolled total synthesis of (+)-bengamide E
J Chem Soc Perkin Trans 1, (2849):
[9] An efficient and convenient approach to the total synthesis of sphingofungin
Liu, DG
Wang, B
Lin, GQ
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26): : 9114 - 9119
[10] A Modular Approach to the Antifungal Sphingofungin Family: Concise Total Synthesis of Sphingofungin A and C
Raguz, Luka
Peng, Chia-Chi
Kaiser, Marcel
Gorls, Helmar
Beemelmanns, Christine
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (05)

← 1 2 3 4 5 →