1725-03-7Relevant articles and documents
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Nimitz,Wollenberg
, p. 3523 (1978)
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Davies et al.
, p. 1351,1355 (1954)
THE FACILE SYNTHESIS OF A LARGE RING LACTONE BY ACID-CATALYSED CYCLISATION OF AN (Z)-ENE-DIYNE HYDROXY ACID PRECURSOR.
Guillerm, Danielle,Linstrumelle, Gerard
, p. 3811 - 3812 (1985)
A large ring lactone is obtained in good yield by acid catalysed cyclisation of the ο-hydroxy acid precursor.
Ynamide-Mediated Macrolactonization
Wang, Xuewei,Yang, Ming,Zhao, Junfeng
, p. 5230 - 5235 (2020/05/27)
Macrolactonization represents a long-standing challenge for organic chemists. Herein, an ynamide-mediated macrolactonization of seco-acids with the assistance of an acid catalyst is described. Various macrolactones ranging in ring size from medium to large can be prepared by using this method. The notorious issues associated with conventional macrolactonization reactions, such as the racemization/epimerization of seco-acids containing an α-chirality center, and the E/Z isomerization of α,β-unsaturated seco-acids can be avoided using this method. In addition, the ynamide-mediated two-step macrolactonization reaction can be performed in a one-pot manner, thus offering a user-friendly protocol. Cyclodepsipeptides containing both amide and ester bonds can also be constructed using this method as the key step to facilitate the ring closure. The total synthesis of dehydroxy LI-F04a, which contains a cyclic hexadepsipeptide core, has been accomplished using this method.
Macrolactonization of Alkynyl Alcohol through Rh(I)/Yb(III) Catalysis
Zhang, Wen-Wen,Gao, Tao-Tao,Xu, Li-Jin,Li, Bi-Jie
supporting information, p. 6534 - 6538 (2018/10/20)
A catalytic macrolactonization through oxidative cyclization of alkynyl alcohol by synergistic transition-metal and Lewis-acid catalysis was developed. Because the alkynyl alcohol substrates involved in this method are different from the seco acids that are used in conventional macrolactonization methods, the current method provides a strategically distinct entry to macrolactones. In addition to the operational simplicity, this macrolactonization protocol proceeds at relatively high concentration, precluding the need for high dilution or slow addition procedures.