Abstract
The title compound, C20H28O3, known as ‘trichodermaerin’ [systematic name: (4E)-4,9,15,16,16-pentamethyl-6-oxatetracyclo[10.3.1.01,10.05,9]hexadec-4-ene-7,13-dione], is a diterpene lactone which was isolated from Trichoderma asperellum. The structure has a tetracycic 6–5–7–5 ring system, with the cyclohexanone ring adopting a twisted half-chair conformation and the cyclopentane ring adopting a half-chair conformation, whereas the cycloheptene and tetrahydrofurananone rings are in chair and envelope (with the methyl-substituted C atom as the flap) conformations, respectively. The three-dimensional architecture is stabilized by C—H⋯O interactions.
Highlights
The title compound, C20H28O3, known as ‘trichodermaerin’ [systematic name: (4E)-4,9,15,16,16-pentamethyl-6-oxatetracyclo[10.3.1.01,10.05,9]hexadec-4-ene-7,13-dione], is a diterpene lactone which was isolated from Trichoderma asperellum
The structure has a tetracycic 6–5–7–5 ring system, with the cyclohexanone ring adopting a twisted half-chair conformation and the cyclopentane ring adopting a half-chair conformation, whereas the cycloheptene and tetrahydrofurananone rings are in chair and envelope conformations, respectively
Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x+1, y+1/2, −z+1; (iii) x, y−1, z
Summary
Suchada Chantrapromma,a*‡ Chotika Jeerapong,b Worrapong Phupong,b Ching Kheng Quahc and Hoong-Kun Func§. Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.002 A; R factor = 0.026; wR factor = 0.069; data-to-parameter ratio = 11.8. The title compound, C20H28O3, known as ‘trichodermaerin’ [systematic name: (4E)-4,9,15,16,16-pentamethyl-6-oxatetracyclo[10.3.1.01,10.05,9]hexadec-4-ene-7,13-dione], is a diterpene lactone which was isolated from Trichoderma asperellum. The structure has a tetracycic 6–5–7–5 ring system, with the cyclohexanone ring adopting a twisted half-chair conformation and the cyclopentane ring adopting a half-chair conformation, whereas the cycloheptene and tetrahydrofurananone rings are in chair and envelope (with the methylsubstituted C atom as the flap) conformations, respectively. The three-dimensional architecture is stabilized by C—HÁ Á ÁO interactions
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