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Volumn , Issue 17, 2007, Pages 2679-2682

Studies towards the synthesis of lindenene: Unexpected stereochemical outcome of an intramolecular cyclopropanation reaction and synthesis of (±)-epi-lindenene and (±)-iso-lindenene

(6) Fenlon, Thomas W a Schwaebisch, Dirk a Mayweg, Alexander V W a Lee, Victor a Adlington, Robert M a Baldwin, Jack E a

a UNIVERSITY OF OXFORD (United Kingdom)

Author keywords

Cyclopropanation; Furanosesquiterpene; Hagemann's ester; Isomerisation; Julia Kocienski methylenation

Indexed keywords

ESTER DERIVATIVE; KETONE DERIVATIVE; LINDENENE; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLOPROPANATION; ISOMERIZATION; POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 35648978174 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-991069 Document Type: Article

Times cited : (37)

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- Spectral data for epi-lindenene (12, IR (thin film, 3075, 3005, 2923, 1658, 1451, 1088, 868 cm-1. 1H NMR (400 MHz, CDCl3, δ, 0.65-0.71 (1 H, m, 0.89-0.93 (1 H, m, 1.13 (3 H, s, CH3, 1.47-1.51 (1 H, m, 1.84-1.90 (1 H, m, 1.94 (3 H, s, CH3, 2.00-2.03 (1 H, m, 2.41-2.43 (1 H, m, 2.44-2.47 (2 H, m, 2.61 (1 H, d, J, 11.5 Hz, 4.48 (1 H, s, R2C=CH2, 4.91 (1 H, s, R2C=CH2, 7.03 (1 H, s, 13C NMR (100 MHz, CDCl3, δ, 8.19, 10.35, 15.93, 21.73, 23.33, 30.67, 34.12, 39.60, 41.09, 101.52, 114.16, 119.47, 136.96, 148.48, 152.56. HRMS ESI, m/z [M, Na, calcd for C15H 18NaO: 237.1250; found: 237.1250
- 18NaO: 237.1250; found: 237.1250.

17
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- Spectral data for iso-lindenene (13, 1H NMR (400 MHz, CDCl3, δ, 0.64-0.70 (1 H, m, 0.88 (3 H, s, CH 3, 0.89-0.95 (1 H, m, 1.44-1.49 (1 H, m, 1.85-1.89 (1 H, m, 1.93 (3 H, s, CH3, 1.96-2.00 (2 H, m, 2.47-2.52 (2 H, m, 2.66 (1 H, d, J, 15.5 Hz, 4.66 (1 H, s, R2C=CH2, 4.98 (1 H, s, 7.09 (1 H, s, 13C NMR (100 MHz, CDCl3, δ, 8.10, 9.92, 17.96, 20.24, 23.10, 28.27, 34.62, 40.74, 42.04, 102.34, 117.37, 119.75, 137.55, 151.34, 152.21. HRMS ESI, m/z [M, Na, calcd for C15H18NaO: 237.1250; found: 237.1250
- 18NaO: 237.1250; found: 237.1250.

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