1973
DOI: 10.1071/ch9730215
|View full text |Cite
|
Sign up to set email alerts
|

Diterpenoids. XXXII. Labda-8,14-dien-13β-ol

Abstract: The 13s compound 13-epiisomanool (labda-8,14-dien-138-01) has been synthesized and its optical rotation compared with that of the 13R isomer (isomanool) in order to correct errors in the literature.The 13s compound labda-8,14-dien-13P-01 (1) has been reported1 (" 13-epiisomanool") to be an oil, [a], -I-27.5" ([4], $80). The rotation of this compound, reputedly lower than that of the 13R epimer (2) ("isomanool"), was used erroneously to assign the C 13 stereochemistry to a number of compounds in this series.$ T… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2

Citation Types

1
10
0

Year Published

1975
1975
2017
2017

Publication Types

Select...
8
1

Relationship

0
9

Authors

Journals

citations
Cited by 17 publications
(11 citation statements)
references
References 0 publications
1
10
0
Order By: Relevance
“…Given that KgTS does not alter the decalin ring core structure, this further indicates that the DTC product has the same C9 and C10 configuration as normal CPP ( 3 ). Accordingly, the SsSS product is (9 R ,10 S )-labda-7,14-dien-13-ol ( 31 ), which has been previously reported (Carman et al, 1973), and the KgTS product is (9 R ,10 S )-labda-7,13(16),14-triene ( 32 ), which also has been previously reported (Maskovic et al, 2013). However, biosynthetic routes to 31 and 32 were not previously known.…”
Section: Resultssupporting
confidence: 73%
“…Given that KgTS does not alter the decalin ring core structure, this further indicates that the DTC product has the same C9 and C10 configuration as normal CPP ( 3 ). Accordingly, the SsSS product is (9 R ,10 S )-labda-7,14-dien-13-ol ( 31 ), which has been previously reported (Carman et al, 1973), and the KgTS product is (9 R ,10 S )-labda-7,13(16),14-triene ( 32 ), which also has been previously reported (Maskovic et al, 2013). However, biosynthetic routes to 31 and 32 were not previously known.…”
Section: Resultssupporting
confidence: 73%
“…The structures (Figure 1) of the resulting compounds; sahandinone (1, 1.0 g), 12-deoxysalvipisone (2, 20 mg) (Jassbi et al 2006), miltirone (3, 750 mg) (Hayashi et al 1970;Houlihan et al 1985), 7α-acetoxyroyleanone (4, 100 mg) (Tezuka et al 1998), labda-7,14-diene-13-ol (5, 10 mg) (Carman et al 1973;Wu & Asakawa 1987;Jassbi et al 2002) were elucidated using spectral data including EI-MS, 1 H-and APT-13 C NMR, HSQC, COSY and HMBC and with comparison with the abovementioned literature data. The structure of compound 5 was elucidated by comparing its Downloaded by [University of Cambridge] at 17:32 17 June 2016 mass and NMR spectral data with those reported in the literature (Carman et al 1973;Wu & Asakawa 1987;Jassbi et al 2002).…”
Section: Resultsmentioning
confidence: 99%
“…Moreover, (13S)-hydroxy-8,14-labdadiene (8) [12][13][14], entverticillol (9), ent-12-epi-verticillol (10), ent-isoverticillenol (11) and ent-verticillanediol (12) [15] were isolated. Their physical and spectral data were identical with those of references data and/or authentic samples.…”
mentioning
confidence: 99%
“…1) collected in Oita pref. resulted in the isolation of a new labdane diterpenoid 13-hydroxy-8,14-labdadien-17-al (14), and known cuparene-type sesquiterpene ketoalcohol, rosulantol (13) [16], (+)-(9S*,13R*)-dihydroxylabda-8(17),14-diene (15) [17], 13-hydroxy-7-oxo-labda-8,14-diene (16) [18], and ent-13-epi-sclareol (17) [19]. Their structures were determined by comparison of the spectral data of the isolated compounds with those of the references.…”
mentioning
confidence: 99%