ChemInform Abstract: Spirastrellolides C to G: Macrolides Obtained from the Marine Sponge Spirastrella coccinea.

Williams, David E.; Keyzers, Robert A.; Warabi, Kaoru; Desjardine, Kelsey; Riffell, Jenna L.; Roberge, Michel; Andersen, Raymond J.

doi:10.1002/chin.200817219

Cited by 2 publications

(2 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…10 The most abundant congener, spirastrellolide A (1) (isolated as the corresponding methyl ester) exhibits striking structural complexity, containing 20 stereocentres, a 38-membered macrolactone and a nine-carbon side chain featuring a (Z,E)-1,4-diene. [11][12][13][14][15] The macrocycle itself contains a tetrahydropyran (A ring), a bicyclic 6,6spiroacetal (BC rings) and a tricyclic 5,6,6-spiroacetal (DEF rings) featuring a chlorine atom at C28. Additionally, spirastrellolide A was found to exhibit potent antimitotic properties via selective protein phosphatase 2A inhibition (IC 50 = 1 nM).…”

Section: Spirastrellolide a Methyl Estermentioning

confidence: 99%

Challenges and discoveries in the total synthesis of complex polyketide natural products

Paterson¹,

Lam²

2017

J Antibiot

View full text Add to dashboard Cite

Structurally complex polyketide natural products, isolated from a variety of marine and terrestrial sources, continue to provide a valuable source of rewarding targets for the synthetic chemist to tackle. In this account, we provide an overview of the total synthesis of several structurally fascinating polyketides with promising anticancer activity completed in our group based on our versatile asymmetric aldol methodology-spirastrellolide A methyl ester, leiodermatolide, rhizopodin and chivosazole F-and highlight the unanticipated challenges and discoveries encountered.

show abstract

Section: Spirastrellolide a Methyl Estermentioning

confidence: 99%

Challenges and discoveries in the total synthesis of complex polyketide natural products

Paterson¹,

Lam²

2017

J Antibiot

View full text Add to dashboard Cite

show abstract

“…The absolute stereochemistry with regard to the biological activity is still unknown, although all 4 possible stereoisomers have been synthesized. [8][9][10][11][12][13][14] More complex structures with bicyclic 1,6-dioxaspiro [4.5]decane ring system and spiro (R)-as well as spiro (S)-configuration are found in the following natural products: (1) (+)-monensin A 2, a polyether ionophorous antibiotic and formed as a metabolite in a biosynthesis of Streptomyces cinnamonensis bacteria 15-18 ; (2) (−)-berkelic acid 3, a novel spiroketal and unique secondary metabolite with selective anticancer activity isolated from an extremophilic Penicillium species 19-25 ; (3) spirastrellolide F, a potent antimitotic agent of the marine sponge Spirastrella coccinea, whose structure has been characterized after methylation as (+)-methyl ester 4 [26][27][28][29][30] ; and (4) (−)-calyculin A 5, a toxin blocking calcium influx and inhibiting protein Ser/Thr phosphatase isolated from the marine sponge Discodermia calyx. [31][32][33][34] Biological studies disclosed that the spiroacetal framework is essential for biological activity in these types of natural compounds.…”

mentioning

confidence: 99%

Stereoselective Synthesis of 1,6,9-Tri-oxaspiro[4.5]decanes From d-Glucose: Novel Structural Motifs of Spiroacetal Natural Products

Cuny

2020

Natural Product Communications

View full text Add to dashboard Cite

Spiroacetals are the central structural core element of numerous natural products and are essential for their biological activity. A typical structural representative of a spiroacetal is the bicyclic 1,6-dioxaspiro[4.5]decane ring system. It represents the complete or partial structure of many biologically potent natural products such as the Paravespula pheromone 1, the antibiotic (+)-monensin A 2, the anticancer agent (−)-berkelic acid 3, the antimitotic ingredient spirastrellolide F, characterized after methylation as (+)-methyl ester 4, and the marine toxin (−)-calyculin A 5. In these compounds, the 1,6-dioxaspiro[4.5]decane ring system is found in either spiro ( R)-6 or ( S) - 6 configuration. The corresponding 1,6,9-trioxaspiro[4.5]decane framework ( S)-7 and ( R)-7 with opposite chirality at the spiro center due to an additional oxygen atom at position 9 in the pyran portion has so far not been found in living organisms or been synthesized. To close this gap and enable structure–activity relationship studies, potentially leading to novel antibiotics and selective anticancer agents, we have developed an efficient and stereocontrolled route to the ( R)- and ( S)-configurated 1,6,9-trioxaspiro[4.5]decane ring system leading to oxa analog motifs of the above natural products.

show abstract

ChemInform Abstract: Spirastrellolides C to G: Macrolides Obtained from the Marine Sponge Spirastrella coccinea.

Abstract: Marine Sponge Spirastrella coccinea. -(WILLIAMS, D. E.; KEYZERS, R. A.; WARABI, K.; DESJARDINE, K.; RIFFELL, J. L.; ROBERGE, M.; ANDERSEN*, R. J.; J. Org. Chem. 72 (2007) 25, 9842-9845; Dep. Chem., Univ. British Columbia, Vancouver, B. C. V6T 1Z1, Can.; Eng.) -Jannicke

Cited by 2 publications

References 1 publication

Challenges and discoveries in the total synthesis of complex polyketide natural products

Challenges and discoveries in the total synthesis of complex polyketide natural products

Stereoselective Synthesis of 1,6,9-Tri-oxaspiro[4.5]decanes From d-Glucose: Novel Structural Motifs of Spiroacetal Natural Products

Contact Info

Product

Resources

About