cas 131929-60-7, SPINOSAD | Articles data

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Total Synthesis of (-)-Spinosyn A via Carbonylative Macrolactonization
Spinosyn A (1), a complex natural product featuring a unique 5,6,5,12-fused tetracyclic core structure, is the major component of spinosad, an organic insecticide and an FDA-approved agent used worldwide. Herein, we report an efficient total synthesis of (-)-spinosyn A with 15 steps in the longest linear sequence and 23 steps total from readily available compounds 14 and 23. The synthetic approach features several important catalytic transformations including a chiral amine-catalyzed intramolecular Diels-Alder reaction to afford 22 in excellent diastereoselectivity, a one-step gold-catalyzed propargylic acetate rearrangement to convert 28 to α-iodoenone 31, an unprecedented palladium-catalyzed carbonylative Heck macrolactonization to form the 5,12-fused macrolactone in one step, and a gold-catalyzed Yu glycosylation to install the challenging β-forosamine. This total synthesis is highly convergent and modular, thus offering opportunities to synthesize spinosyn analogues in order to address the emerging cross-resistance problems.
Bai, Yu,Shen, Xingyu,Li, Yong,Dai, Mingji
p. 10838 - 10841
(2016/09/12)

Total synthesis of spinosyn A. 2. Degradation studies involving the pure factor and its complete reconstitution
A total synthesis of natural levorotatory spinosyn A (1) has been achieved. The first objective, to confirm the absolute configurational assignment of tricyclic ketone 2 prepared earlier, was accomplished by oxidative degradation of the macrocyclic lactone ring in 1. The route began with the implementation of a four-step one-pot process that resulted in the efficient conversion of 6 into 18. A combination of periodate cleavage and peracid oxidation events then led to 2. In the reconstruction phase, a Pd- catalyzed coupling of a vinylstannane with an acid chloride reestablished the great majority of the structure in an enantiocontrolled manner. Once macrolactonization had been effected, the 2,3,4-tri-O-methylrhamnose unit was introduced first with exceptionally good stereocontrol. The final glycosidation, which involved a 2-mercaptopyrimidine derivative of D- forosamine, was met with an expectedly diminished percentage of the desired β-anomer.
Paquette, Leo A.,Collado, Iván,Purdie, Mark
p. 2553 - 2562
(2007/10/03)

Chemical Properties

Melting Point: 84oC to 99.5oC
Boiling Point: 801.515 °C at 760 mmHg
Flash Point:438.541 °C
Density: 1.167 g/cm³
Solubility:Soluble in DMSO
Vapor Pressure: 0mmHg at 25°C
Refractive Index: 1.54
PKA: Spinosyn A: 8.1 (base); Spinosyn D: 7.8 (base)
PSA: 111.22000
LogP: 5.48740

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Chemical Properties

Melting Point: 84oC to 99.5oC

Boiling Point: 801.515 °C at 760 mmHg

Flash Point:438.541 °C

Density: 1.167 g/cm³

Solubility:Soluble in DMSO

Vapor Pressure: 0mmHg at 25°C

Refractive Index: 1.54

PKA: Spinosyn A: 8.1 (base); Spinosyn D: 7.8 (base)

PSA: 111.22000

LogP: 5.48740

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131929-60-7

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Chemical Properties

Melting Point: 84oC to 99.5oC

Boiling Point: 801.515 °C at 760 mmHg

Flash Point:438.541 °C

Density: 1.167 g/cm3

Solubility:Soluble in DMSO

Vapor Pressure: 0mmHg at 25°C

Refractive Index: 1.54

PKA: Spinosyn A: 8.1 (base); Spinosyn D: 7.8 (base)

PSA: 111.22000

LogP: 5.48740

Global suppliers and manufacturers of 131929-60-7total 100 suppliers on LookChem

Density: 1.167 g/cm³