کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5229574 | 1383666 | 2007 | 12 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: A concise route to the C3-C23 fragment of the macrolide palmerolide A A concise route to the C3-C23 fragment of the macrolide palmerolide A](/preview/png/5229574.png)
A concise route to the C3-C23 part of the macrolide palmerolide A was developed. This part features the 7,10,11-trihydroxy sector containing the 8E-double bond as well as the 14,16-diene subunit. The stereocenter at C-7 originated from a Noyori reduction on alkynone 8. The substrate 16 containing an enyne was obtained via a Claisen rearrangement. The vicinal diol at C10,C11 was created by a Sharpless asymmetric dihydroxylation. After selective protecting group manipulations the propargylic alcohol was reduced with Red-Al to the E-alkylic alcohol 26. The conjugated diene in the fragment 40 resulted from a Stille cross-coupling reaction between the vinylstannane derived from alkyne 30 and the vinyl iodide 39. The latter could conveniently be prepared by an aldol/Wittig strategy.
Journal: Tetrahedron - Volume 63, Issue 52, 24 December 2007, Pages 13006-13017