Synthetic studies on a phenyl-laulimalide analogue

Faveau, Christelle; Mondon, Martine; Gesson, Jean‐Pierre; Mahnke, Tobias; Gebhardt, Sandra; Koert, Ulrich

doi:10.1016/j.tetlet.2006.09.104

Cited by 30 publications

(14 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…More recently, Koert and Gesson have exploited the TiCl 4 -promoted conjugate addition of an allylsilane toward the synthesis of laulimalide analogues. 15 The stereochemistry obtained in their reaction was reported to converge with the results initially reported by Wu.…”

Section: Figuresupporting

confidence: 75%

Asymmetric Conjugate Addition of Crotylstannane: Synthesis of (-)-Lasiol

Wilding¹,

Gregg²,

Mullins³

2010

Synlett

View full text Add to dashboard Cite

Lasiol, the major component of the mandibular gland secretion, serves as the primary sex attractant of the male ant, Lasius meridionalis. Our interest in lasiol stems from the stereochemistry of the chiral methyl substituents and the synthetic challenges posed by this common structural motif. As such, an asymmetric 1,4-conjugate addition of an allylic stannane to produce the 1,2-anti-dimethyl arrangement with high stereocontrol has resulted in the synthesis of (-)-lasiol.

show abstract

Section: Figuresupporting

confidence: 75%

Asymmetric Conjugate Addition of Crotylstannane: Synthesis of (-)-Lasiol

Wilding¹,

Gregg²,

Mullins³

2010

Synlett

View full text Add to dashboard Cite

show abstract

“…18 In addition, five different teams seeking to broaden the understanding of cytotoxicity structure activity relationships (CSAR) have prepared 35 synthetic congeners of 2. 4,14,[19][20][21][22][23][24][25][26][27] None of the synthetic analogs obtained to date have exhibited greater in vitro cytotoxicty in comparison to 2. The powerful cytotoxin neolaulimalide (3) represents the only additional natural product related to 1 and 2 described, ever.…”

Section: Introductionmentioning

confidence: 99%

Sponge-Derived Fijianolide Polyketide Class: Further Evaluation of Their Structural and Cytotoxicity Properties

et al. 2007

View full text Add to dashboard Cite

The sponge-derived polyketide macrolides fijianolides A (1) and B (2), isolaulimalide and laulimalide, have taxol-like microtubule-stabilizing activity, and the latter exhibits potent cytotoxicity. Insight on the biogeographical and phenotypic variations of Cacospongia mycofijiensis is presented that will enable a future study of the biosynthetic pathway that produces the fijianolides. In addition to fijianolides A and B, six new fijianolides, D-I (7-12), were isolated, each with modifications to the C-20 side chain of the macrolide ring. Compounds 7-12 exhibited a range of in vitro activities against HCT-116 and MDA-MB-435 cell lines. Fijianolides 8 and 10 were shown to disrupt interphase and mitotic division, but were less potent than 2. An in vivo evaluation of 2 using tumor-bearing severe combined immuno-deficiency mice demonstrated significant inhibition of growth in HCT-116 tumors over 28 days.

show abstract

“…3,40,41 With over 150 different monomers, PHA are a rich source of chiral hydroxyalkanoic acids. 43 3-hydroxyoctanoic acid (3HO) exhibits potential antimicrobial activities 44 ; 3HO is also an intermediate for statins known as HMG-CoA reductase inhibitors. MCL 3HA have shown potential to be pharmaceuticals of high value.…”

Section: Monomers As Chiral Intermediatesmentioning

confidence: 99%