Enediynes synthesis through desulfurdimerizaton of propargylic dithioacetals
Journal
Phosphorus, Sulfur, and Silicon and the Related Elements
Start Page
1-7
ISSN
1042-6507
1563-5325
Date Issued
2024-10-22
Author(s)
Hsian-Rong Tseng
Abstract
Two novel methods for transforming of propargylic dithioacetals into the corresponding enediynes are described. The first method involves the initial reaction of a propargylic dithioacetal with nBu2CuLi followed by transmetalation with ZnBr2, to generate an allenylzinc intermediate. Subsequent introduction of MeI and a catalytic quantity of Pd(PPh3)4 leads to the formation of the dimeric enediyne in moderate yield. In addition, 2,5-dithia-nonane is isolated in 73% yield, arising from the transformation of the sulfur moiety from propargylic dithioacetals. Alternatively, the second method employs two equivalents of Cp2Ti[P(OEt)3]2 to react with propargylic dithioacetals, yielding enediynes satisfactorily. The reaction can proceed either inter- or intramolecularly. © 2024 Taylor & Francis Group, LLC.
Subjects
desulfurdimerization
enediynes
Propargyl dithioacetals
SDGs
Publisher
Informa UK Limited
Type
journal article