Modular Enantioselective Synthesis of 8-Aza-prostaglandin E1

被引：13
作者：
Wang, Xiao-Gang
Wang, Ai-E
Hao, Yi
Ruan, Yuan-Ping
Huang, Pei-Qiang [1 ]
机构：
[1] Xiamen Univ, Dept Chem, Xiamen 361005, Fujian, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 18期
关键词：
INTERMOLECULAR ADDITION-REACTIONS; ASYMMETRIC-SYNTHESIS; RECEPTOR AGONISTS; METHYL-ESTER; PROSTAGLANDIN; EP4; DISCOVERY; ANALOGS; POTENT; CONSTRUCTION;
D O I：
10.1021/jo401412g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report herein for the first time the enantioselective synthesis of 8-aza-PGE(1). The synthesis used the cross olefin metathesis reaction to connect the 5-vinyl-gamma-lactam subunit, prepared from (R)-malic acid via the Ley's sulfone-based alpha-amidalkylation protocol (dr = 6.8:1), with the chiral pre-omega-chain. The latter was synthesized in high enantioselectivity from (E)-2-octenol by the Sharpless asymmetric epoxidation and the titanocene-mediated epoxide opening. This modular approach is quite concise and flexible, and requires only eight steps from commercially available reagents.
引用
收藏
页码：9488 / 9493
页数：6
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  • [1] [Anonymous], 2010, J CHEM EDUC, V87, P1348
  • [2] Catalytic enantioselective synthesis of prostaglandin E1 methyl ester using a tandem 1,4-addition-aldol reaction to a cyclopenten-3,5-dione monoacetal
    Arnold, LA
    Naasz, R
    Minnaard, AJ
    Feringa, BL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (24) : 5841 - 5842
  • [3] Design and synthesis of novel bone-targeting dual-action pro-drugs for the treatment and reversal of osteoporosis
    Arns, Steve
    Gibe, Romelo
    Moreau, Anne
    Morshed, M. Monzur
    Young, Robert N.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (06) : 2131 - 2140
  • [4] SYNTHESIS OF AN 11-DEOXY-8-AZAPROSTAGLANDIN-E1 INTERMEDIATE
    BARCO, A
    BENETTI, S
    POLLINI, GP
    BARALDI, PG
    SIMONI, D
    VICENTINI, CB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10) : 1734 - 1736
  • [5] STEREOSELECTIVE SYNTHESIS OF STATIN ANALOGS
    BERNARDI, A
    MICHELI, F
    POTENZA, D
    SCOLASTICO, C
    VILLA, R
    [J]. TETRAHEDRON LETTERS, 1990, 31 (34) : 4949 - 4952
  • [6] SYNTHETIC ROUTES TO CHIRAL 3-PYRROLIDINOLS
    BHAT, KL
    FLANAGAN, DM
    JOULLIE, MM
    [J]. SYNTHETIC COMMUNICATIONS, 1985, 15 (07) : 587 - 598
  • [7] Discovery of a potent and selective agonist of the prostaglandin EP4 receptor
    Billot, X
    Chateauneuf, A
    Chauret, N
    Denis, D
    Greig, G
    Mathieu, MC
    Metters, KM
    Slipetz, DM
    Young, RN
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (06) : 1129 - 1132
  • [8] SUBSTITUTION-REACTIONS OF 2-PHENYLSULFONYL-PIPERIDINES AND 2-PHENYLSULFONYL-PYRROLIDINES WITH CARBON NUCLEOPHILES - SYNTHESIS OF THE PYRROLIDINE ALKALOIDS NORRUSPOLINE AND RUSPOLINONE
    BROWN, DS
    CHARREAU, P
    HANSSON, T
    LEY, SV
    [J]. TETRAHEDRON, 1991, 47 (07) : 1311 - 1328
  • [9] Discovery of highly selective EP4 receptor agonists that stimulate new bone formation and restore bone mass in ovariectomized rats
    Cameron, KO
    Lefker, BA
    Chu-Moyer, MY
    Crawford, DT
    Jardine, PD
    DeNinno, SL
    Gilbert, S
    Grasser, WA
    Ke, HZ
    Lu, BH
    Owen, TA
    Paralkar, VM
    Qi, H
    Scott, DO
    Thompson, DD
    Tjoa, CM
    Zawistoski, MP
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (07) : 1799 - 1802
  • [10] A general model for selectivity in olefin cross metathesis
    Chatterjee, AK
    Choi, TL
    Sanders, DP
    Grubbs, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) : 11360 - 11370
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