Total synthesis of dimeric pyrrole-imidazole alkaloids.

More About This Textbook


This thesis describes the synthesis of the dimeric pyrrole-imidazole alkaloids sceptrin, ageliferin, nagelamide E, oxysceptrin, nakamuric acid, nakamuric acid methyl ester, axineallamine A, and axinellamine B. The total synthesis of racemic sceptrin was accomplished by the fragmentation of an oxaquadricyclane to establish the cyclobutane core, followed by attachment of the pyrrole sidechains and elaboration of the 2-aminoimidazole units. Microwave irradiation of sceptrin yielded the natural products ageliferin and nagelamide E. An enantioselective synthesis of sceptrin was effected by means of an enzymatic desymmetrization and careful modification of the oxaquadricyclane fragmentation conditions. The absolute configuration of ageliferin was determined by synthesis from enantiopure sceptrin, highlighting the possibility that sceptrin may be the biosynthetic precursor of ageliferin. A computational study of the formation of ageliferin indicates that this reaction likely proceeds via a radical fragmentation mechanism. Biosynthetic considerations led to the synthesis of oxysceptrin, nakamuric acid, and nakamuric acid methyl ester from sceptrin. Attempts to obtain the cyclopentyl core of the axinellamines, massadines, and palau'amines culminated in the development of a ring contraction of ageliferin. However, the stereochemistry of the spiro ring junction formed in this reaction was opposite that found in the natural products. Finally, the total synthesis of axinellamines A and B by closure of a linear intermediate and studies on oxidation of intermediates formed in this route are discussed.
Read More Show Less

Product Details

  • ISBN-13: 9780549650911
  • Publisher: ProQuest LLC
  • Sold by: Barnes & Noble
  • Format: eTextbook
  • Pages: 278
  • File size: 117 MB
  • Note: This product may take a few minutes to download.

Customer Reviews

Be the first to write a review
( 0 )
Rating Distribution

5 Star


4 Star


3 Star


2 Star


1 Star


Your Rating:

Your Name: Create a Pen Name or

Barnes & Review Rules

Our reader reviews allow you to share your comments on titles you liked, or didn't, with others. By submitting an online review, you are representing to Barnes & that all information contained in your review is original and accurate in all respects, and that the submission of such content by you and the posting of such content by Barnes & does not and will not violate the rights of any third party. Please follow the rules below to help ensure that your review can be posted.

Reviews by Our Customers Under the Age of 13

We highly value and respect everyone's opinion concerning the titles we offer. However, we cannot allow persons under the age of 13 to have accounts at or to post customer reviews. Please see our Terms of Use for more details.

What to exclude from your review:

Please do not write about reviews, commentary, or information posted on the product page. If you see any errors in the information on the product page, please send us an email.

Reviews should not contain any of the following:

  • - HTML tags, profanity, obscenities, vulgarities, or comments that defame anyone
  • - Time-sensitive information such as tour dates, signings, lectures, etc.
  • - Single-word reviews. Other people will read your review to discover why you liked or didn't like the title. Be descriptive.
  • - Comments focusing on the author or that may ruin the ending for others
  • - Phone numbers, addresses, URLs
  • - Pricing and availability information or alternative ordering information
  • - Advertisements or commercial solicitation


  • - By submitting a review, you grant to Barnes & and its sublicensees the royalty-free, perpetual, irrevocable right and license to use the review in accordance with the Barnes & Terms of Use.
  • - Barnes & reserves the right not to post any review -- particularly those that do not follow the terms and conditions of these Rules. Barnes & also reserves the right to remove any review at any time without notice.
  • - See Terms of Use for other conditions and disclaimers.
Search for Products You'd Like to Recommend

Recommend other products that relate to your review. Just search for them below and share!

Create a Pen Name

Your Pen Name is your unique identity on It will appear on the reviews you write and other website activities. Your Pen Name cannot be edited, changed or deleted once submitted.

Your Pen Name can be any combination of alphanumeric characters (plus - and _), and must be at least two characters long.

Continue Anonymously

    If you find inappropriate content, please report it to Barnes & Noble
    Why is this product inappropriate?
    Comments (optional)