Synthesis of the C1-C16 fragment of ionomycin using a neutral (η3-allyl)iron complex

被引:15
|
作者
Cooksey, John P. [1 ]
Kocienski, Philip J. [1 ]
Li, Ying-fa [1 ]
Schunk, Stefan [1 ]
Snaddon, Thomas N. [1 ]
机构
[1] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1039/b606262h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Key steps in the synthesis of the C1 - C16 polyketide fragment of ionomycin were the nucleophilic addition of an organocuprate to a neutral (eta(3)-allyl) iron complex and the construction of a beta-diketone moiety by the Rh-catalysed rearrangement of an alpha-diazo-beta-hydroxyketone.
引用
收藏
页码:3325 / 3336
页数:12
相关论文
共 50 条
  • [21] ORGN 732-Towards the synthesis of Rhizoxine D: A stereo selective synthesis of C1-C16 core
    Iqbal, Javed
    Padakanti, Srinivas
    Pal, Manojit
    Mukkanti, K.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
  • [22] SYNTHESIS OF BRYOSTATINS .1. CONSTRUCTION OF THE C(1)-C(16) FRAGMENT
    BLANCHETTE, MA
    MALAMAS, MS
    NANTZ, MH
    ROBERTS, JC
    SOMFAI, P
    WHRITENOUR, DC
    MASAMUNE, S
    KAGEYAMA, M
    TAMURA, T
    JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12): : 2817 - 2825
  • [23] An approach towards the C1-C16 fragment of antineoplastic macrolide bryostatins by kinetic resolution of a racemic terminal epoxide using Jacobsen's catalyst
    Yadav, JS
    Bandyopadhyay, A
    Kunwar, AC
    TETRAHEDRON LETTERS, 2001, 42 (29) : 4907 - 4911
  • [24] Synthesis of the C(1)-C(16) fragment of bryostatins using an 'ene' reaction between an allylsilane and an alkynone
    O'Brien, Matthew
    Thomas, Eric J.
    TETRAHEDRON, 2011, 67 (52) : 10068 - 10081
  • [25] Synthesis of the C-1-C-16 fragment of the marine toxin, laulimalide
    Shimizu, A
    Nishiyama, S
    TETRAHEDRON LETTERS, 1997, 38 (34) : 6011 - 6014
  • [26] TOTAL SYNTHESIS OF THE IONOPHORE ANTIBIOTIC IONOMYCIN - ASYMMETRIC-SYNTHESIS OF THE C1-C10 AND C-11-C16 SYNTHONS
    EVANS, DA
    DOW, RL
    TETRAHEDRON LETTERS, 1986, 27 (09) : 1007 - 1010
  • [27] Synthesis of the bryostatin 1 northern hemisphere (C1-C16) via desymmetrization by ketalization/ring-closing metathesis
    Voight, EA
    Seradi, H
    Roethle, PA
    Burke, SD
    ORGANIC LETTERS, 2004, 6 (22) : 4045 - 4048
  • [28] Assessment of Gaussian-3 and density functional theories for enthalpies of formation of C1-C16 alkanes
    Redfern, PC
    Zapol, P
    Curtiss, LA
    Raghavachari, K
    JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (24): : 5850 - 5854
  • [29] Stereoselective Synthesis of the C(1)-C(28) Fragment of Amphidinol 3
    Yadav, Jhillu S.
    Gopalarao, Yerragorla
    Chandrakanth, Dandekar
    Reddy, Basi V. Subba
    HELVETICA CHIMICA ACTA, 2016, 99 (06) : 436 - 446
  • [30] A Convergent Synthesis of the C1-C16 Segment of Goniodomin A via Palladium-Catalyzed Organostannane-Thioester Coupling
    Fuwa, Haruhiko
    Nakajima, Motohiro
    Shi, Jinglu
    Takeda, Yoshiyuki
    Saito, Tomoyuki
    Sasaki, Makoto
    ORGANIC LETTERS, 2011, 13 (05) : 1106 - 1109