Pseudoaglycone of spinosyn a

Area of Science:

• Organic Chemistry
• Crystallography
• Natural Products Chemistry

Background:

• Spinosyn A is a widely used insecticide derived from the bacterium Saccharopolyspora spinosa.
• Understanding the chemical transformations and structural properties of Spinosyn A derivatives is crucial for developing new pest control agents.

Purpose of the Study:

• To characterize the compound obtained by hydrolysis of Spinosyn A.
• To elucidate the three-dimensional structure and intermolecular interactions of the title compound in the crystalline state.

Main Methods:

• Chemical hydrolysis of Spinosyn A.
• Single-crystal X-ray diffraction analysis to determine molecular and crystal structure.
• Conformational analysis of the fused ring system.
• Identification of hydrogen bonding networks (O-H⋯O and C-H⋯O).

Main Results:

• The title compound, 9-ethyl-13-hydroxy-14-methyl-2-(3,4,5-trimethoxy-6-methyl-tetrahydro-2H-pyran-2-yl-oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione (C33H50O9), was successfully synthesized.
• The fused cyclopentene ring exhibits a twisted conformation, while the fused cyclohexene and cyclopentane rings adopt envelope conformations.
• Intermolecular hydrogen bonds (O-H⋯O and C-H⋯O) form a layered crystal structure parallel to the ab plane.

Conclusions:

• The hydrolysis of Spinosyn A yields a structurally distinct compound with defined conformational preferences.
• The crystal packing is stabilized by a network of hydrogen bonds, providing insights into solid-state behavior.
• Structural characterization aids in understanding the structure-activity relationships of spinosyn derivatives.