Synthesis and Absolute Configuration of Three Natural ent‐Halimanolides with Biological Activity.

Abstract

Terpenes Terpenes U 0200 Synthesis and Absolute Configuration of Three Natural ent-Halimanolides with Biological Activity. -Preliminary tests reveal that (I) exhibits cytotoxic and antiviral activity. -(MARCOS*, I. S.; PEDRERO, A. B.; SEXMERO, M. J.; DIEZ, D.; BASABE, P.; HERMANDEZ, F. A.; URONES, J. G.; Tetrahedron Lett. 44 (2003) 2, 369-372; Dep. Quim. Org., Fac. Cienc. Quim., Univ. Salamanca, E-37008 Salamanca, Spain; Eng.) -Lindner 15-182

Tandem-, Domino- and One-Pot Reactions Involving Wittig- and Horner-Wadsworth-Emmons Olefination

“…The prospects of multi-step, one-pot reactions and reaction cascades incorporating Wittig reagents can be seen in the rich chemistry of ketenylidenetriphenylphosphorane (178) (Scheme 45) [182][183][184][185], which has been reviewed earlier [182,186,187]. Lastly, catalytic Wittig reactions can be seen as a subset of tandem reactions involving phosphoranes.…”

Halimanes and cancer: ent-halimic acid as a starting material for the synthesis of antitumor drugs

“…This group is characterized by a cyclic side chain consisting of a butenolide or γ-hydroxybutenolide framework ( Figure 4 ), which shows the following result: • Ent -halimanolide 40 showed cytotoxicity at micromolar levels against HeLa (5.0 µM) and MDCK (5.1 µM) cell lines ( Marcos et al, 2003b ). • Echinohalimane A 41 exhibited cytotoxicity toward a variety of hematologic and solid tumor cell lines, showing better results for the latter ones including MOLT-4 (2.1 μg/mL), HL-60 (2.1 μg/mL), DLD-1 (0.96 μg/mL), and LoVo (0.56 μg/mL) cell lines ( Chung et al, 2012 ).…”

“…• Ent -halimanolide 40 showed cytotoxicity at micromolar levels against HeLa (5.0 µM) and MDCK (5.1 µM) cell lines ( Marcos et al, 2003b ).…”

“…The synthesis of 40 , 61 , and 63 ( Hara et al, 1995 ) using ent -halimic acid methyl ester 59 as a starting material is performed according to the route showed in Scheme 1 ( Marcos et al, 2003b ; Marcos et al, 2005b ).…”

Synthetic Studies Towards the ent-Labdane Diterpenoids: Rearrangement of ent-Halimanes

“…) is a bicyclic diterpene that has been used as a starting material for the synthesis of different bioactive molecules such as the ent-halimanolides [1], chettaphanin I and chettaphanin II [2], (+)-agelasine C [3] and sesterterpenolides with an disydiolane skeleton [4].…”