444809-41-0Relevant academic research and scientific papers
Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach
Wang, Jingjing,Ting, Samuel Z. Y.,Harvey, Joanne E.
supporting information, p. 1815 - 1822 (2016/04/10)
Bestmann ylide [(triphenylphosphoranylidene)ketene] acts as a chemical linchpin that links nucleophilic entities, such as alcohols or amines, with carbonyl moieties to produce unsaturated esters and amides, respectively. In this work, the formation of α,β
Formation of chiral C(sp3)-C(sp) bond by allylic substitution of secondary allylic picolinates and alkynyl copper reagents
Kiyotsuka, Yohei,Kobayashi, Yuichi
supporting information; experimental part, p. 7489 - 7495 (2010/01/06)
(Chemical Equation Presented) To establish allylic substitution of secondary allylic alcohol derivatives with alkynyl copper reagents, allylic esters bearing the (2-pyridine)CO2-, (2-pyrazine)CO2-, (EtO)2PO2-, C6F5CO2-, o-(Ph2P)-C6H4CO2-, MeOCO 2-, or. AcO- group were examined. First, picolinate (R 1=Me, R2=CH2OPMB) was subjected to reaction with (TMS-C≡C)2CuLi 3 LiBr at 0 °C. Although no substitution took place, MgBr2 (3 equiv) was found to promote the reaction to produce the anti SN2′ product in 93% yield with 94% regioselectivity and 99% chirality transfer. In contrast, substitution of the other esters with the copper reagent in the presence of MgBr2 were less reactive ((2-pyrazine)CO2-) or marginally reactive (other cases). Generality of the substitution using picolinates was established with five picolinates (R1=Me, Ph(CH2)2, PMBO(CH 2)3; R2=Me, CH2OPMB, CH 2OTBS, C5H11, c-C6H11) and seven alkynyl copper reagents (R3=TMS, Ph, p-TBSOC 6H4, p- and o-MeOC6H4, p-MeC 6H4, p-FC6H4), furnishing anti SN2′ products in 61-93% yields with high regioselectivity (usually >90%) and high chirality transfer (usually >95%). In addition, transformation of the products was briefly studied. 2009 American Chemical Society.
A study toward a total synthesis of fostriecin
Kiyotsuka, Yohei,Igarashi, Junji,Kobayashi, Yuichi
, p. 2725 - 2729 (2007/10/03)
In order to synthesize the major C(3)-C(12) part of fostriecin, asymmetric dihydroxylation of several dienes 5a-f, prepared by cross-coupling reactions of several types, was studied, thus providing high dependency on the hydroxyl groups at C(5) and C(11). The best regioselectivity was obtained with 5d to produce diol 23, which was later transformed into the advanced intermediate 26.
