Toward the total synthesis of scytophycins: Synthesis of the C7-C21 fragments of scytophycins A, B, and C

被引：1

作者：

Ohyoshi, Takayuki ^{[1
]}

Namiki, Mayu ^{[1
]}

Miyazaki, Yuto ^{[1
]}

Sato, Shusei ^{[1
]}

Noguchi, Tomonari ^{[1
]}

Kigoshi, Hideo ^{[1
]}

机构：

[1] Univ Tsukuba, Fac Pure & Appl Sci, Dept Chem, 1-1-1 Tennodai, Tsukuba, Ibaraki 3058571, Japan

来源：

TETRAHEDRON LETTERS | 2023年 / 114卷

关键词：

Scytophycins; Cytotoxic macrolide; Diversity-oriented synthesis; Epoxidation; 4-Reduction; CONJUGATE REDUCTION; C(1)-C(18) SEGMENT; COUPLING REACTION; CHLORIDE; AGENTS;

D O I：

10.1016/j.tetlet.2022.154250

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Scytophysins are cytotoxic macrolides with a 22-membered ring and are characterized by their strong cytotoxicities targeting cytoskeletal protein actin. Toward the comprehensive total synthesis of scytophycins, we have investigated the late-state functionalization using fragment compounds. We established stereoselective construction of the C7-C21 part in scytophycins A and B involving characteristic C16 epoxide by using Sharpless epoxidation. Although stereoselectivity remains unsatisfactory, reduction of the C16 exo-olefin for the synthesis of scytophycin C was achieved.(c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：5

共 50 条

[41] Toward the Total Synthesis of Amphidinolide N: Synthesis of the C8-C29 Fragment
Kawashima, Yuki
Toyoshima, Atsushi
Fuwa, Haruhiko
Sasaki, Makoto
ORGANIC LETTERS, 2016, 18 (09) : 2232 - 2235
[42] Synthesis of the C11-C21 and C13-C21 fragments of epothilones from D-glucose
Lee, HW
Lee, IYC
Hong, YD
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2000, 21 (12) : 1177 - 1178
[43] Studies on the total synthesis of macrolactin A.: A stereoselective synthesis of the C3-C13 and C14-C24 fragments
Li, SK
Xu, R
Bai, DL
TETRAHEDRON LETTERS, 2000, 41 (18) : 3463 - 3466
[44] Toward the synthesis of spirastrellolide B: A synthesis of the C1-C23 subunit
Keaton, Katie A.
Phillips, Andrew J.
ORGANIC LETTERS, 2008, 10 (06) : 1083 - 1086
[45] Total Synthesis of Biselyngbyolide B and Its C21-C22 Z-Isomer
Kaemmler, Lena
Maier, Martin E.
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (08): : 4554 - 4567
[46] Toward the total synthesis of patellazole B: synthesis of an advanced C1-C25 fragment corresponding to the macrocyclic skeleton
Phillips, Andrew W.
Anketell, Matthew J.
Balan, Tudor
Lam, Nelson Y. S.
Williams, Simon
Paterson, Ian
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (37) : 8286 - 8291
[47] Toward a total synthesis of an aglycone of spiramycin; A chiron approach to the C-1/C-4 and the C-13/C-15 fragments
Breuilles, P
Oddon, G
Uguen, D
TETRAHEDRON LETTERS, 1997, 38 (37) : 6607 - 6610
[48] Stereoselective total synthesis of Pestalotioprolide C and C7-epi-Pestalotioprolide C
Jami, Pradeep Kumar
Battula, Sreenivasa Rao
Parimi, Uma Devi
Syed, Tasqeeruddin
SYNTHETIC COMMUNICATIONS, 2023, 53 (17) : 1391 - 1397
[49] Total synthesis of the proposed azaspiracid-1 structure, part 2: Coupling of the C1-C20, C21-C27, and C28-C40 fragments and completion and synthesis
Nicolaou, KC
Chen, DYK
Li, YW
Qian, WY
Ling, TT
Vyskocil, S
Koftis, TV
Govindasamy, M
Uesaka, N
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) : 3649 - 3653
[50] Studies directed towards the total synthesis of polyether antibiotic ionomycin: asymmetric synthesis of fragments C(24)-C(32) and C(1)-C(23)
Yadav, J. S.
Yadav, Nagendra Nath
Reddy, B. V. Subba
TETRAHEDRON, 2015, 71 (40) : 7539 - 7549

← 1 2 3 4 5 →