156953-84-3Relevant articles and documents
A Matteson Homologation-Based Synthesis of Doliculide and Derivatives
Tost, Markus,Andler, Oliver,Kazmaier, Uli
, p. 6459 - 6471 (2021/12/17)
Doliculide belongs to a group of marine cyclodepsipeptides with interesting biological properties. Apart from a halogenated dipeptide, a polyketide fragment containing 5 stereogenic centers is the most eye-catching element. This building block can be synthesized in a highly stereoselective fashion using only one key reaction: the Matteson homologation. This straightforward protocol allows for the introduction of a wide range of substituents at almost any position of a growing carbon chain and it is therefore perfectly suited for the synthesis of derivatives for structure-activity relationship studies.
Enantioselective Total Synthesis of (?)-Doliculide Using Catalytic Asymmetric Hydrogenations
Che, Wen,Wen, Danyang C.,Zhu, Shou-Fei,Zhou, Qi-Lin
, (2019/03/19)
A concise and efficient strategy has been developed to construct a polyketide chain by employing relay asymmetric hydrogenations catalyzed by two chiral spiro iridium catalysts. By using this strategy, an enantioselective total synthesis of (?)-doliculide
Directed hydrogenations and an Ireland-Claisen rearrangement linked to Evans-Tishchenko chemistry: The highly efficient total synthesis of the marine cyclodepsipeptide doliculide
Chen, Tao,Altmann, Karl-Heinz
, p. 8403 - 8407 (2015/06/02)
Two new convergent total syntheses have been developed for the cytotoxic, actin microfilament-stabilizing marine cyclodepsipeptide doliculide (1). A key strategic element of both routes is the establishment of the central stereogenic center of the characteristic polydeoxypropionate stereotriad by means of a hydroxyl-directed catalytic hydrogenation of a trisubstituted double bond. The requisite olefin substrates were obtained through a modified Suzuki-Miyaura coupling or through Ireland-Claisen rearrangement of a propionate ester, respectively; the latter was the direct result of a highly selective Evans-Tishchenko reduction of a hydroxy ketone that had been obtained in a stereoselective Paterson aldol reaction. Doliculide (1) was finally obtained in a total number of 17 or 15 (14) linear steps, respectively, which represents a substantial improvement over previous syntheses of this highly bioactive natural product.
Total synthesis of antitumor depsipeptide (-)-doliculide.
Ghosh,Liu
, p. 635 - 638 (2007/10/03)
[reaction: see text] (-)-Doliculide, a potent antitumor agent, is synthesized stereoselectively in a convergent manner. The key strategy involves a stereoselective synthesis of the polyketide unit and synthesis of the D-tyrosine derivative, followed by as
Total Synthesis of Doliculide, a Potent Cytotoxic Cyclodepsipeptide from the Japanese Sea Hare Dolabella auricularia
Ishiwata, Hiroyuki,Sone, Hiroki,Kigoshi, Hideo,Yamada, Kiyoyuki
, p. 4712 - 4713 (2007/10/02)
The total synthesis of doliculide (1), a potent cytotoxic cyclodepsipeptide from the Japanese sea hare, has been achieved.
Enantioselective Total Synthesis of Doliculide, a Potent Cytotoxic Cyclodepsipeptide of Marine Origin and Structure-Cytotoxicity Relationships of Synthetic Doliculide Congeners
Ishiwata, Hiroyuki,Sone, Hiroki,Kigoshi, Hideo,Yamada, Kiyoyuki
, p. 12853 - 12882 (2007/10/02)
The total synthesis of doliculide (1), a potent cytotoxic cyclodepsipeptide from the Japanese sea hare Dolabella auricularia, has been achieved.The key step of the synthesis is the construction of the sereogenic centers of a 15-carbon polyketide-derived d
