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Tetrahedron Letters

Volumn 43, Issue 31, 2002, Pages 5479-5481

Mechanism of clerosterol biosynthesis in Ajuga hairy roots: Stereochemistry of C-28 methylation of 24-methylene sterol

(3) Koami, Takeshi a Ohyama, Kiyoshi a Fujimoto, Yoshinori a

a TOKYO INSTITUTE OF TECHNOLOGY (Japan)

Author keywords

2H NMR; Biosynthesis; Clerosterol; Clionasterol; Stereochemistry; Steroids and sterols

Indexed keywords

CLEROSTEROL; CLIONASTEROL; STEROL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CHEMICAL MODIFICATION; DEUTERON NUCLEAR MAGNETIC RESONANCE; METHYLATION; NONHUMAN; PLANT ROOT; PROTON TRANSPORT; STEREOCHEMISTRY;

AJUGA; AJUGA REPTANS;

EID: 0037194182 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(02)01061-4 Document Type: Article

Times cited : (1)

References (16)

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- 3), 2.77 (1H, m, 6-H), 3.32 (3H, s, OMe), 3.94 (1H, m, 28-H).

14
- 0005771443
- 3) δ: 11.86 (C-18), 12.21 (C-29), 18.83 (C-21), 18.96 (C-27), 19.39 (C-19), 19.63 (C-26), 21.08 (C-11), 24.31 (C-15), 26.37 (C-23), 28.24 (C-16), 28.95 (C-25), 31.67 (C-2), 31.91 (C-7), 31.91 (C-8), 33.90 (C-22), 36.27 (C-20), 36.51 (C-10), 37.26 (C-1), 39.78 (C-12), 42.31 (C-4), 42.31 (C-13), 45.97 (C-24), 50.14 (C-9), 56.03 (C-17), 56.77 (C-14), 71.82 (C-3), 121.72 (C-6), 140.77 (C-5). A signal of C-28 (δ 23.1 for non-labeled compound) was negligible.

15
- 0005723797
- 3), 2.77 (1H, m, 6-H), 3.33 (3H, s, OMe), 3.80 (1H, m, 28-H).

16
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- 3) δ: 11.85 (C-18), 12.19 (C-29), 18.83 (C-21), 18.99 (C-27), 19.39 (C-19), 19.58 (C-26), 21.08 (C-11), 24.31 (C-15), 26.35 (C-23), 28.23 (C-16), 28.94 (C-25), 31.67 (C-2), 31.91 (C-7), 31.91 (C-8), 33.93 (C-22), 36.27 (C-20), 36.51 (C-10), 37.26 (C-1), 39.78 (C-12), 42.31 (C-4), 42.31 (C-13), 45.97 (C-24), 50.14 (C-9), 56.03 (C-17), 56.77 (C-14), 71.82 (C-3), 121.72 (C-6), 140.76 (C-5). A signal of C-28 was negligible.

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